


Salty Sweet

by secondstar



Category: Teen Wolf (TV)
Genre: Age Difference, Alternate Universe - Human, Artist Derek, Butt Plugs, Coming Untouched, Consensual Somnophilia, Deepthroating, First Time, Intercrural Sex, Jock Straps, M/M, Masturbation, Phone Sex, Porn, Porn store AU, Power Bottom Derek, Rimming, Sex Swing, Sex Toys, Shower Sex, Switching, Tattooed Derek, Underage Drinking, Versatile Stiles Stilinski, Voyeurism, amatuer porn
Language: English
Status: Completed
Published: 2014-03-08
Updated: 2014-04-26
Packaged: 2018-01-14 23:48:43
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 11
Words: 46,478
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1283308
Author URL: https://archiveofourown.org/users/secondstar/pseuds/secondstar
Summary: <blockquote class="userstuff">
              <p>Derek works at a porn store. One day, Stiles comes in asking all sorts of TMI questions about different toys. That's where it all starts.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> NGL I am in love with this fic. This may or may not be the most self indulgent thing I have ever written. Anything not realistic re: the porn store is my bad. 
> 
> beta'd by lauren, mel, bk, and beth.
> 
> blame Hoechlin wearing those glasses to the 300 premiere the reason Derek has glasses in this okay? okay. 
> 
> let me know if I didn't tag something correctly, please! 
> 
> rated M for now, rating changes in chapter 2 to E.
> 
> date: please do not REPOST this fic anywhere else without my consent. Please do not put it on GoodReads that is a site for PUBLISHED works, not fic.

Working the day shift at an adult store wasn’t all it was cracked up to be, if Derek was perfectly honest with himself. He spent most of his mornings restocking shelves, checking prices, and tuning his Pandora playlists to his liking. 

There was a buzzer that went off whenever someone wanted to enter the store. Everyone had to be ID’ed before coming in because, by law, the store was eighteen and up. Derek had to stop stocking the shelves, he had a box of vibrators he was hanging up, in order to let someone in. Derek hopped behind the counter instead of using the swinging door, which was on the other side of the room, sliding across it and landing with a thump in front of the plexiglass window that separated them like a movie theatre box office. 

“ID,” Derek said with a sigh, his hand out, waiting for it. 

“Uh, sure,” the guy -- no, the kid said from the other side of the window. Derek straightened his glasses as he looked him over. Obviously high school, with a comic book shirt -- Green Lantern, nice choice -- and a plaid over shirt, along with a hoodie, and Converse. Typical. The kid had a buzz cut, which made him look barely old enough to drive. Derek held back a laugh as he watched him struggle to get his driver’s license out of his wallet in order to hand it over. 

There was no way Derek was letting the kid get in with a fake ID. None. When he finally slid his ID towards Derek, he looked up at him, his eyes going wide for a second. Derek arched an eyebrow, but said nothing as he looked down at the ID. It didn’t look fake, had the right holographics and it was obviously the same kid. Derek looked him over one more time, his eyes narrowing as he thought maybe it was an older brother’s ID or something. His brow furrowed when he chanced a glance at the name. 

“How long does this usually take?” The kid asked, his voice deeper than Derek thought it would be. Derek snorted, handing the ID back to him. 

“Happy Birthday,” Derek said as he hit the buzzer, unlocking the door for whatever-the-fuck his name is, shit could not be said out loud in the English language. Surprisingly, What’s His Name grinned at him, his brown-eyed gaze not leaving Derek’s for a moment. 

“Thanks,” he said before he opened the door, stepping inside the store. There were a few people milling about, a homeless guy that liked perusing the DVD selection, a soccer mom who seemed to be undecided on which Bullet to purchase, and Derek’s Tuesday regular, George. 

Derek decided to walk around the counter this time, instead of jumping over it as he made his way back to restocking. Derek’s situational awareness of the customers was pretty spot-on. The soccer mom caved and left without buying the Bullet she had in her hand for about three minutes, obviously wavering between her own pleasure and thinking about her husband, since she worried at her wedding ring as soon as she put it down -- in the wrong fucking spot. 

George loitered, but Derek knew he would, as did the homeless man. Derek didn’t care if people stuck around, especially on a cooler day, it wasn’t like he had something else to do. 

What’s His Name, though, walked around the entire store three times before Derek sighed, putting the empty box down on the counter before walking up to him as he worried at his bottom lip. 

“Can I help you with something?” Derek asked as he slid his hands into his back pockets, attempting to give the kid a helpful expression. Wide-eyed, he shook his head, then wavered. 

“It’s pretty TMI,” he said, his eyes casting across the aisle of lubricating options. Derek tried not to laugh as he nodded his head. 

“Shoot,” he said with a shrug. He had no one else to talk to, might as well see if he could help the kid. 

“How the fuck am I supposed to pick which one of these to use? It’s like picking a toothpaste. They all say the same damn thing--”

“What are you using it for?” Derek asked. He got a gaping mouth in reply, which, wow, that mouth opened wide. Derek shook his head, looking away towards the options before them. “It depends on what you’re using it for.”

“Well, that’s the thing--”

“Are you using lotion?” Derek asked incredulously. He remembered being that young, using lotion instead of lube because what teen wants to tell their mom they need it. 

“Uh, KY?” he said.

Derek smiled, rolling his eyes as he handed over a bottle labelled SILK. 

“This is better,” Derek said, about to turn away.

“Does it work for anal, too?” 

Derek stopped where he was, looking the kid up and down one more time. He hadn’t expected that-- but you can never tell, really. 

“Depends on what you’re doing,” Derek said truthfully. “It’s a good product, I use it, but not for anal play, unless it’s just fingers, for toys I’d suggest--” Derek stopped talking when he saw the look the kid was giving him. “What?”

“Um, fingers is what I meant.” 

Derek gave him a smile, nodding his head. 

“Use that, then. It will change your world.”

“I’m sure,” he laughed. 

“Is that all you wanted to get?” Derek asked him. “I can check you out if you’re ready.” What’s His Name visibly swallowed, which distracted Derek for a moment, as he looked around the store. 

“I don’t know what half of this stuff his for. I mean, porn, yeah, I get... but what exactly is a Tenga Cup?”

“It’s basically... a toy that you stick your dick in and it feels like you’re getting deep throated.”

“Jesus,” he said, looking back towards where Derek knew they kept them. “Is it like a Fleshlight?”

“Not quite,” Derek said with a wry smile. “It has suction, it isn’t something to fuck into.”

“Ah,” he said, swallowing again when his voice caught in his throat. “I think I might--”

“You should,” Derek said, nodding his head as he walked over to the very thing they discussed. He tossed it to the kid. “You won’t regret it.”

“Do you have one?” he asked. Derek almost told him that was a little personal, but he couldn’t fault him for asking. 

“Nah,” Derek said with ease. “But it’s rated pretty damn well on Amazon.” 

“Huh,” he said as he examined the box. “Okay.”

“You ready?” Derek asked as he shoved his hand in his back pocket again. What’s His Name’s gaze was on his arm, which wasn’t surprising considering that there was a full tattoo sleeve on it, along with another half one on his other arm. They distracted people easily, and Derek was used to it. Derek snapped his fingers, bringing attention back to him. He leaned forward a bit, the corner of his mouth lifting as his eyes met What’s His Name’s. “You want to look around some more?”

“I think I’m good,” he said as he followed Derek to the counter. Derek rang the items up, then put them in a brown paper bag. 

“Totally doesn’t look suspicious at all,” he laughed as he handed Derek wadded up bills to pay with. 

“Want me to put it in a clear bag for you?” Derek asked, teasing him. The way that the kid’s cheeks reddened had Derek coughing back his reaction as blood flowed down between his legs. His cheeks were splotchy, red only below the cheekbone. That, paired with how red his lips were from biting them, had Derek’s mind heading straight for the gutter. “How do you say your name?” Derek asked as he handed him back the change. 

“Just call me Stiles,” he said with a small smile. “It’s easier that way.” Derek nodded, knowing that he probably wouldn’t see him again, or that he wouldn’t remember if he did. 

“Have fun, Stiles,” Derek said, grabbing the empty box as Stiles walked out with his new toy. 

-

Derek definitely remembered Stiles when he showed up again two weeks later. It was nighttime, busier than during the day, and Derek was manning the door and cash register as Erica, the other employee on duty, helped out on the floor. Currently, she leaned against the counter, bored despite the fact they had eleven people roaming around. 

“ID,” Derek said, because he had to, even though he knew exactly who Stiles was. He wore a Batman shirt, along with a different plaid shirt on top of it this time. Stiles handed it over easily, taking it out of his back pocket. “Had it ready?” Derek asked with a smirk. 

“Yeah,” Stiles said, avoiding Derek’s gaze. Derek lifted an eyebrow but said nothing as he slid the ID back, then buzzed him in. 

“Let me know if you have any questions,” Derek called out. Erica gave him a look because he never said that. Derek shrugged, then spun around on the sole barstool they had, in order to change the Pandora station.

Stiles disappeared into the store as Derek spun around in the chair, tilting his head back as he waited for someone to check out. Erica slid over, her eyes narrow as she looked at him. 

“What?” Derek asked, his tone put-upon. 

“What was that about?” Erica asked, as she motioned towards Stiles. Derek sighed audibly, his eyes rolling as he turned towards her, his hands in his lap. 

“What was what about, Erica?” 

“The twink,” Erica said with a grin. Derek stood up, plastering on a fake smile as a customer came up with, wow, seven DVDs. Derek didn’t judge, but why buy DVDs when there was the internet? Derek gave Erica a look, trying to tell her telepathically that she should do her fucking job, as he rang up the total for the pile o’porn. 

When Derek was done, he looked around the store for Erica and for Stiles. He craned his neck until he saw them, together, in the corner, near the dildos. Oh, hell no, Erica wasn’t going to--

Derek left the counter behind, walking up to them. 

“Erica, you’re on phone duty.”

“Bullshit,” she said, her arms crossing. “You are.”

“Who’s the assistant manager?”

“Your mom’s chest hair,” Erica said before she stalked off towards the counter, leaving Derek and Stiles alone. Stiles, again, wasn’t looking at Derek. Maybe he would rather talk to Erica, after all. 

“Do you want to talk with Erica?” Derek asked him. 

Stiles shook his head, his eyes finally meeting Derek’s. 

“No, I’d rather talk to you.”

“What about?” Derek asked, taking a step closer. Stiles shrugged as he shoved his hands into his front pockets. 

“Well, for starters, that lube is phenomenal.” 

Derek smirked at him. “Miles better than lotion.”

“And KY,” Stiles said as he licked his lips. 

“I see you’re perusing the anal toys, having some second thoughts about only fingers?” Derek asked, way too casually considering the topic of conversation. Stiles covered his mouth, probably to hide a smile, but Derek didn’t care. He was too used to talking about sex to be bothered by it. 

“Yeah,” Stiles said, his voice lower than it had been two moments ago. Derek couldn’t help but smile at him, really, because of how flustered he seemed to be. 

“What did you have in mind?” Derek asked simply. Stiles gestured to the dildos he was standing by. “Ah.”

“Yeah,” Stiles said, laughing as he ran his fingers through his hair.   
“Have you ever--”

“No,” Stiles said, cutting Derek off. “I mean, yes? But the one I got was way too big, like I couldn’t even-- it hurt and I read that it really shouldn’t with proper prep so that’s why I’m here? I mean, I’ve used my fingers, you know? But they cramp? And the angle is weird,” Stiles said, using hand gestures, which wow, that needed to stop. “I don’t know.”

“Yeah, okay,” Derek said, taking another step closer, putting a hand on Stiles’ back, patting it before turning him towards the merchandise. “First, you have to clean up, so we’ll get you a kit.”

“Really? For like, myself?” Stiles asked, clearly perplexed. 

Derek raised his eyebrows, then nodded his head slowly. 

“Yeah, really. So I’ll set you up, it’ll be fine.”

Derek really didn’t have time for this, really, he didn’t, but Stiles’ genuine inquiries intrigued him a little more than he knew it should. 

“Do you know what size you started with?” Derek asked. 

“Nine inch,” Stiles said with an uneasy smile. Derek blanched. No wonder, poor kid. Going from awkward fingering to a nine-inch dildo, which was pretty fucking thick-- 

Derek shook his head. 

“Right,” Derek said, trying for reassuring. Stiles looked at Derek’s arms again, this time lingering on the intricate details. Derek let him. 

“Do you think I should get something with like, a suction cup on it? Would that help? Because the one I bought is like, rubbery and flops around a lot. Should I use plastic or silicone? Would the suction cup like, look weird? Not that it matters how it looks because I’d just be by myself but I mean, does it look weird?” Stiles asked, taking a breath afterwards from rambling. Derek was about to answer when he heard a whistle coming from the front desk.

“Derek! A little help here,” Erica called out across the store. Derek lifted his head, from where he had been watching Stiles articulate his questions with his hands, to see Erica inundated with customers. He sighed, turning back towards Stiles. 

“Start small,” Derek said with a grin before walking away from him. “I’m serious,” he called out over his shoulder. 

By the time Stiles came up to the line, some twenty minutes later, Erica almost checked him out. With one look from Derek, though, she backed off. The store was still busy, and with the two of them behind the counter, that meant no one was out on the floor. Erica went, but not without flipping her hair defiantly. 

This time, Stiles paid with a debit card. 

“Did you find everything you were looking for?” Derek asked with a quirk of his lips. Stiles smiled as he bit his lip, nodding his head. 

“I think so,” he whispered. Derek appraised his choices. He made a gesture at the three-set of butt plugs in varying sizes. 

“Ambitious,” Derek said. 

“Price made more sense than buying them separate,” Stiles said as he coughed, looking away from Derek. “Obviously, I’m starting small.”

“Obviously,” Derek said, trying to keep his voice even so he didn’t give away the fact that all he could picture was Stiles bent over with the plug up his ass, showing it off for him. He also bought a dildo, thankfully a normal-sized one instead of one of the massive monster cocks that Derek saw him eyeing earlier. 

What a fucking image that was. 

After Derek watched Stiles leave, he avoided Erica’s gaze. He didn’t want to see her judgemental face, because he was reprimanding himself enough for the both of them. Barely eighteen, Derek was almost ten years older than him. Almost being the key word. 

-

Derek worked two jobs. He worked days at the store, where he was assistant manager, with the odd night shift once or twice a week which was usually a double. He worked part-time at a local gallery, where three of his pieces hung on display. He liked working there, mostly because it was also an art studio on the second floor where different artists could rent out space. Derek, since he worked at the gallery, got a reduced rate for his space, practically a steal considering he got first dibs and picked the area nearest the window. 

He worked with mostly charcoals, but he sometimes dabbled with mixed media, which were the pieces that hung in the gallery itself. Next door to the gallery was a coffee house, also locally owned, that attached to the gallery so there was a lot of foot traffic, even at night. 

With a fresh cup of coffee, Derek made himself comfortable for the evening behind the front desk of the gallery. It was set up with a desk, a little lower than the counter itself, so he could draw. Almost everyone that worked at the gallery was an artist, most of them also renting the space upstairs as well, so the fact that there was a desk made especially for them to work during their shifts meant a lot to Derek. 

He sketched for a while, readying a new tattoo design to bring his unfinished sleeve to his elbow, as people walked in and out of the gallery. 

“Are you stalking me?” Someone asked, bringing Derek out of his zone, his pencil stilling over the sketchbook. He pushed his glasses up his nose as he looked up to see Stiles standing there with an iced coffee in his hand, the straw in his mouth, and an incredulous look that Derek was pretty sure would be able to make him come in the shower later when he thought about this moment. 

“I think I should be asking you that,” Derek said, his tone completely dry as he leaned over his sketchbook, hiding it from Stiles’ view because he extended his neck attempting to look. Derek shut it, sliding it away from himself as he tapped the pencil against the desk, leaning on it. “Are you stalking me, Stiles?” 

“What? Nope,” Stiles said, popping the ‘p’ with his lips as he looked around, pointing at two people who were walking around the gallery hand in hand. “I’m here as the official third wheel.” 

Derek fought back the smile that wanted to emerge. Stiles dropped his hand, taking a long sip of his coffee, making a noise with the straw because the drink was almost gone. Stiles shook the drink and sighed, leaning against the counter like they were friends. 

Derek pushed himself away, putting distance between the two of them. Stiles was a customer, a young one at that, and jack-off fantasy or not, Derek had no intentions of stepping over the invisible line. 

“How late is this place open?” Stiles asked him. 

“Depends, usually half hour before the coffee shop closes,” Derek said shuffling papers around for no reason. He glanced towards Stiles’ friends, who seemed to be lost in their own world, then back to Stiles. “So in about an hour.”

“Ugh,” Stiles said, his head tilting back to reveal the long expanse of his neck, his Adam’s apple bobbing up and down as he complained with a groan. “This is killing me.”

“Bored?” Derek found himself asking. 

“So bored, they said it was like, a friend thing, they aren’t dating,” Stiles said, waving a hand at his friends dismissively. “Scott was all ‘come on dude, please’ and ‘it’s not a date I swear’, but obviously--”

“Do you like art?” Derek asked, taking Stiles’ mind off Scott. Stiles shrugged as he shoved his free hand into his hoodie pocket. He chewed on the straw, which distracted Derek, but he caught himself before he stared too long. 

“I mean, it’s cool?” 

“You could take a look around,” Derek suggested. 

“I’d rather talk to you,” Stiles said as he looked towards the door. Derek knew right then that he was fucked, literally. 

“Me? Why?” Derek asked as he scratched at his week’s worth of stubble. Again, Stiles shrugged. 

“You’re really easy to talk to, so hey can I ask you stuff here?” Stiles asked. “Like, about--”

“Sure,” Derek said, his voice lower. “But voices echo in here, so try not to shout about it,” he said, gesturing for Stiles to walk around to the back of the counter. There were two stools to sit at, and against Derek’s better judgement he indicated for Stiles to take one. Stiles scrambled around to a stool, sitting on it with a smile on his face. 

“Awesome. Great. Okay, so, question: do you think if I got a double-ended dildo it would be easier to like, hold onto?” Stiles asked, his teeth gnawing on that damned straw still. Derek blinked slowly, trying to wrap his mind around the fact that Stiles just asked him that. 

“Well, I guess it would be easier--”

“Because I am really like, lanky? And not very flexible. Should I do yoga?” 

“If you want,” Derek said, his mind filling with all sorts of images that were making it hard for him to concentrate. He stalled by taking a sip of his forgotten coffee. 

“I googled different, like, fingering techniques, and one blog said that I should use a vibrator, but I thought those were for girls mostly? Have you ever used one?” Stiles asked, his face completely serious. Derek scoffed as he exhaled, looking around the mostly empty gallery. Stiles’ friends were gone, probably found the supply closet to make out in. Derek ran his hand over his face as he looked towards the ceiling. 

“Yeah, I've used one, and with lube it helps stretch.” 

Stiles beamed at him, his shoulders relaxing. 

“Thanks, man. Seriously. Sometimes the internet lies.” 

Derek laughed. “It does do that, yeah.” 

“So about the vibrator, do they make super quiet ones? Because I don’t live alone, you know? And a dildo doesn’t make a noise.” 

Derek licked his lips after he watched Stiles do the same thing. He sighed, because Stiles was in high school. This was so wrong on so many different levels. 

“They have quiet ones, but they still make noise. If you’re concerned, I’d maybe stick to toys without batteries.” 

Stiles chewed on his bottom lip as he nodded, taking Derek’s every word into consideration. 

“You’re right. I mean, I’ve got stuff. I should just make do with what I have.”

“Do not use that nine-inch dildo,” Derek said, leaning forward with his hands on his thighs. “Until you can take that middle range plug, alright?” Stiles’ cheeks reddened as he nodded his head. 

“Yeah, got it. Start small.” 

“Exactly,” Derek said as Stiles’ friends came into view, leaning on each other. Stiles stood up, running his long, slender fingers over his buzzed hair, winking at Derek before meeting them by the door. 

“See ya,” Stiles said with a wave. 

All Derek could do in response was stare as Stiles walked out the door. 

He was so fucked.


	2. Chapter 2

**Notes for the Chapter:**

> If you feel like I haven't tagged something correctly, please let me know!
> 
> I suggest everyone listen to Salty Sweet by MS MR just saying. A suggestion. 
> 
> Again with the entirety of this fic being self indulgent.

The first thing Stiles did was lock the door to his bedroom. His dad was on duty, would be until morning, so he didn’t necessarily need to lock it, but he felt safer that way. It wasn’t like he was doing something illegal or anything; it was totally legit, what he was doing. 

He paced his room, picking up stray socks and his pajama pants he wore earlier, before he showered. Stiles’ cheeks reddened as he thought about how he readied himself, using the kit he bought from the porn store, from Derek. 

“Okay,” Stiles said, taking a deep breath as he rubbed his fingers over his hair, shaking out his arms. “This is totally okay, it’s gonna be fucking awesome, even,” he said, psyching himself up. “Right.” 

He leaned over his desk, sliding his finger over his mouse pad, waking his computer up. He clicked and typed his way to the porn website he was a member of, had been since he got his own debit card, really. Only now that he was actually eighteen, he could participate. 

It was easy, really, setting up an amatuer stream on their site. Stiles did it twice already, but only jacked off and fingered himself on camera. Interestingly enough, people watched him. Stiles found it mind-boggling that he not only had actual people watch him, but that many messaged wanting to know when he would go on air again. 

This time, Stiles was ready. He had everything set up for a good time, in his opinion. He moved his room around, to the surprise of his dad, the day before, so that his bed was closer to his desk, for easier viewing pleasure. Stiles set the lube and the smallest butt plug down on the desk, ready for use. He read online that he should use a condom on the toy, for easier cleanup, so he bought a box from the drugstore just out of town. 

The shitty thing about having a father as the sheriff in a small town was the fact that everyone gossiped. He didn’t need Sally at the drugstore telling his dad anything about his purchases, especially considering how unbelievably single Stiles was. The last thing Stiles wanted to do was explain why he had a need for them, really, especially to his dad. 

Stiles looked to the clock on his computer, his fingers strumming against the keys idly as he stalled on clicking ‘go live!’ on the website. He looked down at what he was wearing, a plain gray t-shirt and black boxer briefs, and bit his lip. 

“Starting out naked is bad,” Stiles told himself. “Stripping is good.” 

At least, that is what he told himself as he clicked the button. A chat popped up, as well as Stiles’ own face so he could see what everyone else would, if anyone showed up. Stiles wasn’t really sure if they would, but either way he was going to get off, so an attempt at making money was just an added bonus. The ‘Stiles Needs to Go to College’ fund wasn’t nearly as full as it should be, by all accounts, if he wanted to avoid being in debt for the foreseeable future, so why not jack off for cash? 

When the first person popped in, Stiles grinned, lifting an eyebrow. 

“Can you hear me okay?” He asked, his body coming alive as he thought about being watched. The anon in the chat responded with ‘yes.’ Okay, then. “Great, well, I’m going to just do my thing, feel free to comment or whatever.” Stiles clicked on his iTunes, queuing up some music to put on in the background. He didn’t want to jack off in silence. The viewers shot up to almost twenty between Stiles picking an album, making him flush a little bit. He wasn’t going to think about it, really, considering these people were being charged per minute. 

Stiles sat back in his chair so that his entire torso could be viewed, his hand sliding down his chest, past his stomach, towards his crotch where he cupped himself, his fingers outlining his cock. Stiles swallowed as he let his lips fall open as he looked down at himself, sliding his shirt up to reveal his happy trail, his fingers brushing against it before letting his shirt fall back down as he rubbed at himself through the fabric of his briefs. He chanced a glance at the chat box, his eyes catching the words ‘TAKE YOUR SHIRT OFF’ in all caps. Stiles tugged at his shirt, pulling it over his head, tossing it to the side as his hand returned to his crotch. 

Stiles let out a moan as he stroked along the outline of his growing erection. He closed his eyes, thinking about being jacked off by a nameless face, their hand wrapped around him as they whispered in his ear. Stiles shoved his hand down his briefs, pushing the fabric out of the way, revealing the head of his cock to the camera. Stiles opened his eyes, checking how many people there were: seventy-five for seven at night on a fucking Wednesday. Who fucking knew. Stiles laughed to himself as he stood in front of the camera, ridding himself of his briefs completely, stroking his cock close to his computer, fucking into his own fist, the head of his cock showing through as he thrust his hips. 

“God,” Stiles exhaled as he sat back down, reaching for the lube, pumping once to slick his hand up. This time when he stroked downward, his hand glided more easily, slick from the lube. Stiles grinned as he moaned, rolling his hips to meet his own hand as he thought about Derek. 

“Shit,” Stiles gasped as he imagined tattooed arms holding him down, stubble brushing against his thigh, and a hot, wet mouth around his cock. 

“Who wants to see me finger myself?” Stiles asked, slowing his strokes so he didn’t shoot his load too early. He looked at the chat for a moment, seeing that he somehow had two hundred people watching, then reached for the lube again as he turned over in his chair, exposing his ass, holding one cheek to the side with his slicked up hand. He brushed his index finger over his entrance as he rested his cheek against the back of his chair. Awkward angles were fucking awkward. Despite doing yoga when he woke up, he wasn’t bendy enough to get any real depth. He pressed inward, slowly moving his finger in and out. He groaned when he attempted to shove his middle finger in as well but pulled out to apply more lube before going any further. 

This time, his fingers slid in more easily. It helped that he worked himself open that morning, too. He didn’t want them to pay for their time and not get to the good part. Stiles managed to situate himself so that he could stroke his cock, left-handed, as he fingered himself, pushing his cock down so the camera could see as precome dripped from the tip. 

His body flushed with heat as he attempted his third finger, but the angle was too awkward. It was shallow, but with the lube helping ease the way, he managed to at least open himself up that extra bit. When Stiles looked to the chat window again, he saw suggestions in all caps, filthy words about how he looked, how much they wanted to bend him over and fuck him. 

He made sure his stream information stated that he was a virgin, because he knew people were into that sort of thing. His exact wording was something along the lines of ‘never been touched by anyone’s hand but my own’, which was the fucking truth of the matter. Apparently self-pleasure sold, because he had three hundred fifty people watching him. 

Stiles grunted as he pulled out, sticking his ass out, showing off his lube slicked hole. 

“Want to watch me plug myself up for the first time?” He asked with a smirk as he showed the camera the toy. “I bought it the other day, and I think it’ll help me get ready for this monster dildo I have. You know, I tried to go from fingers straight to it, but it was too big,” Stiles said, laughing at himself as he pumped lube into his hand, then spread it around the plug. “I talked with this awesome guy, who was really open with me about questions I had. He said I should work up to it, so I bought these plugs. Anyways, this is the smallest one, let’s see if I can at least get this in.” 

Stiles pushed his chair out of the way so that his bed was in full view. He decided to go on his hands and knees because he tried to go on his back, but again with the not flexible. He pressed his cheek against his mattress, spreading his legs out so his cock, which was admittedly flagging a little bit, hung down between his legs. He stroked himself as he pressed the tip of the plug against his entrance. He rubbed his thumb over the head of his cock as he thrusted the butt plug in and out shallowly, each time pressing in further. He rocked back and forth on his knees, hoping it would help get it in. He twisted it, then moved his hand from his cock to his ass cheek, spreading it to the side. 

Stiles shouted into his comforter when he felt it sink in all the way, the edge of it flush against his ass. Stiles dropped his hands, tucking them both in against his chest as he reveled in the feel of it. The pressure was immense. He felt full, so fucking full, as his entire body throbbed. His erection was back in full force as he rolled his hips. With each movement, Stiles moaned. He was covered in a thin sheen of sweat as he wrapped his hand around his cock once more, rolling onto his back, lifting his legs in the air as he kept them spread. 

He gripped one thigh, keeping his leg in the air as he pushed his cock up away from his precome-smeared stomach, stroking upward. He looked up at the ceiling as he felt his climax building. He thought about how he probably needed a cock ring of some sort, so he could last longer. As soon as he thought about Derek picking one out for him, Stiles shouted out, coming hard.

He stood up, moaning as the butt plug shifted inside of him, rubbing against his prostate. 

“Jesus Christ,” he panted as he held onto his desk, looking at the chat: four hundred people. Stiles showed the camera his come covered hand. “What should I do?” He asked, his cheeks flushed. 

‘Lick it’, someone suggested. Suddenly everyone chimed in with the same response. 

“I’ve never done that before,” Stiles said truthfully. He stuck his tongue out, teasing for a second before he stuck his index finger in his mouth. He tried not to make a face at the salty tang of his own come, but swallowed it down anyway. “I’m sure it’s an acquired taste,” he said with a lift of his eyebrow. 

He turned around, showing off his ass. He looked at himself on the stream, seeing what he looked like to everyone else. His cheeks were red, his body glistening with sweat, his ass spread wide by the plug. He felt his cock stir between his legs, which surprised him because his recovery period usually wasn’t that fast. 

He gripped the base, twisting the plug as he knelt on his chair. He grunted as he attempted to pull it out. His body fought against it as he relaxed, the plug sliding out easily, whimpering almost immediately at the loss. He held on to the plug, bending over farther to make sure everyone could see. Stiles watched more than enough porn to know what they wanted to see: him gaping. Being curious himself, he craned his neck, his jaw dropping at the sight of himself closing back up. He brushed his fingers over his ass, his fingers sliding in easier this time. He retracted them, pressing his index and middle finger to the side, showing off his work. 

When Stiles turned around again, he rested his elbow on the desk, his face close to the camera. 

“That was a lot of fun,” he said. “I hope you guys enjoyed that as much as I did. I think I’m gonna go ahead and say I’m going to do that again,” he laughed, almost running his hand over his face. He stopped though, when he remembered how lubed his fingers were. “Until next time,” he said before signing off. As he clicked ‘offline’ he saw that almost seven hundred people watched him jack off and plug himself up. 

He tried not to think about the voyeuristic aspect of the entire thing, since he barely engaged in conversation with them, but the thought of getting money for what he just did was a little earth-shattering to him. Half the money, or maybe more, he needed to look at the contract again, was for the website itself. But still, he would be getting money. 

His body buzzed as he cleaned up, wiping his hands on the towel before discarding the condom, then putting on his briefs. He washed the plug, then tossed the lube covered towel into the washer before stepping into the shower himself. As soon as he was under the water, Stiles covered his mouth with his hand, laughing to himself because he just came on camera with a plug shoved up his ass. When he got out of the shower, Stiles made himself mac ‘n’ cheese before doing his pile of homework. 

-

Stiles waited over a week before he went back to the porn store. It was in the town over from Beacon Hills, a place called Bradbury, on the outskirts near a bunch of warehouses and a car dealership. He went after school, taking his ID out in his Jeep before going in. He tried not to let the look of disappointment wash over him when he saw Erica at the window instead of Derek. 

“ID,” she said with a coy smile. Stiles handed it over without a word. She looked him over, her eyebrow lifting as she handed it back. “Nice name.”

“Thanks,” Stiles said as she buzzed him in. 

Derek was nowhere in sight, which made Stiles’ stomach drop. He wasn’t even stocking anything around the store. Stiles shoved his hands into his jeans pockets as he made his way towards the BDSM area. He was on a mission, and that mission was cock rings. He wanted to last longer, and he knew that’s what he needed. It would be awesome to order shit like this online, but he and his dad shared Amazon Prime, so that was no good. Also, whenever Stiles got packages in the mail, his dad always asked what everything was. Stiles shook his head as he thought about opening a package with a cock ring in it in front of his dad and having to explain that one. 

No thank you. 

Stiles searched the aisle, his eyes widening when he saw some of the stuff they had stocked. 

“You look lost,” a familiar voice said. Stiles couldn’t stop himself from grinning as he looked up to see Derek on the next aisle over, his arms dangling over the partition. He wore a long-sleeved Henley, dark maroon with the sleeves shoved up to his elbows, revealing half of his tattoos. His stubble seemed shorter than normal, like he trimmed it or shaved recently. Stiles tried not to stumble over his words as he caught Derek’s eyes, almost green through his black-rimmed glasses. 

“I might be a little,” Stiles said as he bit his lip. “Care to help a guy out?” He tried not to freak out as Derek laughed, his head dropping down as he shook his head, pushing himself away from the shelf to walk around to meet Stiles. 

“What’s on today’s list?” Derek asked as he appeared around the corner, wearing the single tightest pair of jeans in existence. They should be fucking illegal, basically. Stiles’ balls drew up at the sight of them as his cock, in turn, throbbed because of the eyeful he got of Derek’s package. 

“Cock rings,” Stiles said, staring. He looked up seconds later to find Derek’s eyebrow lifted towards the ceiling. 

“Really?” 

“Yeah,” Stiles said, clearing his throat. “You know, so I don’t come everywhere after two minutes.” Because it was the fucking truth and he knew it. Derek looked so close to laughing, Stiles almost ran out of the store in embarrassment of his word vomit, but instead Derek tugged on his shirt sleeve, his head jerking for Stiles to follow him. Stiles watched Derek’s ass as they walked around the corner. Stiles almost ran into Derek, because he definitely hadn’t been paying attention to the fact that Derek stopped walking. 

Stiles held his hand out, touching Derek’s back in order to stop himself. 

“Oops,” Stiles said, pulling his hand away and placing it on the back of his neck apologetically. Derek didn’t say anything as he pointed at the cock rings. “Jesus, is that amount of choice like, necessary?” He asked. 

“Probably not, but it’s nice to have a choice.” Derek said with a shrug. “What were you thinking of?” 

“Well, not the one with the spikes, that is like, dangerous to my health,” Stiles said, his fingers grazing the aforementioned ring. 

“Noted,” Derek said, the corner of his mouth lifting upward. 

“I don’t know, just plain black,” Stiles said with a shrug, picking up one and looking at the packaging. “Do these come in sizes or is it one size fits all?” Derek coughed beside him, covering his mouth as he held back a laugh. Stiles smirked to himself, pleased he got that kind of reaction from him. 

“Unless the dildo you bought is the size of your own cock, that should work for you,” Derek said, touching the ring Stiles had in his hands. Stiles reddened, nodding his head. 

“This should work then,” he said. 

“That it?” Derek asked. 

Stiles swayed back and forth, looking anywhere but Derek. 

“Vibrators?” Stiles asked. Derek didn’t say a word as they made their way to the other side of the store. 

“Pink?” Derek asked, pointing to one that looked like a princess wand. 

Stiles snorted. “The glitter is a little over the top for me, despite my love of the color.” 

“No glitter, then,” Derek said, seriously. 

“I’ve no real preference,” Stiles said. “Hey, question though,” Stiles said as he looked over his copious amount of options. “Like, the more crazy ones? Like the rabbit or whatever, you know? Where they move weird and have like, balls and shit that move around-”

“I’d start smooth and not that big,” Derek said, both of his eyebrows raised. “Unless you’ve already moved up?” Stiles looked Derek directly in the eye and shook his head. No, he hadn’t moved up from the small plug yet. “Then let’s stay with smooth for now.”

“Okay,” Stiles said, his stomach in knots over the use of ‘us.’ Derek pointed to a plain blue vibrator, at seven inches, that wasn’t very thick at all. He knocked his knuckle against it, then crossed his arms. 

“I have this one,” he told Stiles as he leaned against the shelf. Blood rushed to Stiles’ crotch as he stared at the vibrator. 

“Okay,” he said, his voice cracking. “It’s gotta be good then, right?” Derek shrugged, his eyes closing momentarily. 

“It will do the job.” 

“I’ll take it, then,” Stiles said. Derek tossed it to him. He caught it easily, but fumbled with it as Derek’s shoulder brushed against his as they walked towards the checkout. Erica was behind the counter, watching both of them approach. Surprisingly, Derek leaned against the counter beside Stiles as Erica rang him up. 

Stiles could practically feel the body heat coming off of Derek, his elbows on the countertop, his fingers linked together as he watched Stiles dig out his wallet. Stiles felt his gaze as he paid Erica, who was quiet throughout the transaction. He willed his erection to calm the fuck down, because it wasn’t the time or the place to jack off, despite the fact that, yeah, technically it sort of was considering they had back rooms for that shit, but still. Stiles didn’t want to touch those with a ten-foot pole. 

“Have a good day,” Erica said, her voice clearly knowing what’s up. Stiles nodded, giving Derek one last look before heading towards the door. As soon as he pushed it open, he heard Derek say, “Shut the fuck up, Erica.” Stiles wanted to think it was something to do with him, but even he knew that probably wouldn’t happen in a million years. 

Derek was older than he was, by at least a handful of years, and damn. Stiles wasn’t selling himself short, not by any means, the money in his bank account gave him reason to stand up a little straighter, despite the dry spell he called high school. But still, Derek was experienced, clearly, and knew what the fuck he was talking about. 

He probably wasn’t even on his radar.


	3. Chapter 3

**Notes for the Chapter:**

> come say hi on [tumblr!](http://attoliancrown.tumblr.com)

Passage of time wasn’t really something that Derek kept track of. Weeks flew by within the blink of an eye to him sometimes, then felt more like a month other times. He didn’t sleep nearly enough, that much he knew, staying up late into the night either hanging out with friends or drawing in his loft. 

Depending on the night of the week, he had different things to do once the gallery closed. Whether it be drinks with friends at a bar, or some shindig at someone’s house, he usually had plans until after midnight, only to show up to his place alone to draw until three or later. The store didn’t open until ten, thankfully, but by the time he had a morning to himself, he usually slept in as much as he possibly could. 

Derek’s friends varied in age, some older artists who ran in the same crowd as the gallery, others were in college, friends of Erica’s and another one of the store's workers, Boyd. One of his best friends was Kyle Parrish, a local deputy he went to high school with. Kyle was a partier, strictly alcohol though, unlike Derek who partook in lighting up once in a while depending on the crowd he was hanging with. 

It was out with Kyle, at a house party, that he ran into Stiles unexpectedly. He saw Stiles, along with his friend from the gallery, from across the hazy room. Kyle had a beer in his hand and was most definitely off duty for the night, not batting an eye at the group of people on the couch passing a bong around. Derek didn’t know what Kyle would do, though, if he found Stiles and his friends with beers in their hands, so he steered Kyle into the kitchen, where he got them both a shot. 

If he hoped Stiles didn’t see him, that thought was quickly dashed by the fact that Stiles walked into the kitchen with a big grin on his face. He was clearly more than a bit buzzed, with his cheeks rosy and eyes glassy. Derek gave Kyle a look but he was in the middle of a conversation with some redhead, so he didn’t say anything as he put his arm around Stiles’ shoulders, steering him back into the living room. 

“I was getting another beer,” Stiles whined, trying to turn around. 

“Here,” Derek said, offering Stiles his own long neck. Stiles took it with a grin. 

“Thanks,” he said as he took a long swig. Derek’s hand slid down Stiles’ back, then to his own back pocket where it was safe from roaming all over his body. 

“You come to these often?” Stiles asked as they found a place to stand where they weren’t surrounded by smoke. 

“Sometimes,” Derek said, watching Stiles’ mouth as he took another drink. “You?” 

“I haven’t been here specifically,” Stiles said, pointing to the floor. “But parties, yes.”

“High school parties,” Derek said, his teeth catching on his bottom lip as Stiles rolled his eyes. 

“So what?”

“So there’s a cop here and I don’t think it would be wise for him to find you and your friends here.”

“Dude, people are smoking over on the couch, I think Scott and I are fine,” Stiles said indignantly. “And you’re talking about Deputy Parrish. I know him.”

“You do?” Derek asked, tilting his head to the side as Stiles worried at his bottom lip, shrugging. 

“Yeah, he works at the station with my dad.”

“Your dad?” Derek parroted. Stiles rolled his eyes again, taking another swig of Derek’s beer. 

“Yeah, my dad, the sheriff.” Derek took the beer from Stiles. “Hey.”

“Nope,” Derek said, drinking the rest of it down, shaking his head as Stiles tried to take it from him. 

“Dick,” Stiles said shoving at him playfully. “I’ll just go get my own.” Derek grabbed hold of Stiles’ wrist, stopping him from leaving, his thumb rubbing against the inside of his wrist, over his pulse before letting go. “I had a nice buzz going.”

“Good for you,” Derek said as he leaned against the wall, his head resting against it as he sighed, looking Stiles over. He should be illegal, Derek surmised. Well, it was good he wasn’t, technically, because then Derek would definitely be fucked. 

He was fucked, actually, because all he could think about was Stiles and that damned cock ring. 

“You haven’t been back,” Derek said. Stiles looked at him, his mouth twitching as he shoved his hands in his back pockets, shrugging with one shoulder as he inched closer. 

“I’ve been busy,” he said slowly, leaning in. Derek breathed in, turning his head away as he pushed off from the wall. He couldn’t do that, not to this kid. That’s what he was -- a kid. Derek had baggage, a lot of it. Stiles didn’t need that weighing him down. 

“I need another,” Derek said, playing off the brush-off. “Want one?”

“What happened to the sheriff’s kid thing?” Stiles asked with a raised eyebrow, shaking off Derek’s dismissal with ease as he followed Derek back to the kitchen. 

“You’re right, water it is.”

“Bullshit,” Stiles said, his hand gripping Derek’s shirt as they waded through the crowd. Derek’s hand slipped behind him instinctively, grabbing hold of Stiles’ hand. He led Stiles into the garage instead of the kitchen, walking into the dark, towards an extra fridge. “Well, then,” Stiles said as Derek dropped his hand in order to open the fridge. He shoved a bottle of water against Stiles’ chest. “Ah,” Stiles mumbled, looking down at the water with realization. Derek tried not to get his hopes up. 

Derek opened another beer, this time a pop top shitty PBR. Stiles glared at him. Derek glared back, his eyes narrowing as he did so. 

“Parrish won’t arrest me,” Stiles said. “He’s bought for me before.” 

Derek snorted, mid sip, covering his mouth; of course Kyle did. 

“Yeah, well, I’m not Kyle.” 

“Don’t I know it,” Stiles said as he played with the label on the bottle of water. Derek swallowed as he indicated with his head for them to head back into the house. Stiles brushed his shoulder against Derek’s as he he headed in first. Derek sighed inwardly as he tried not to watch Stiles’ ass as they walked through the party, separating when Stiles saw Scott at the couch along with the same girl that was with them at the gallery. Derek left them to it, finding Kyle easily enough. He was the DD, so he didn’t drink much else, switching to water after he finished his PBR. 

He left without saying bye to Stiles. It didn’t matter, really, because they weren’t friends. They were acquaintances at most, and as Derek dropped Kyle off at his own apartment, heading back to his loft, alone, Derek realized that maybe, just maybe, that wasn’t all he wanted to be to Stiles. 

-

Derek had his sketchpad with him at the store. He worked with pencil when not at home, it was cleaner than charcoals, but he used the side of the pencil the same way he would charcoal, shading as he zoned out. 

“Derek,” Erica said, snapping her fingers in front of his face, grabbing his attention. “Did you hear what I said?”

“What?” Derek asked as he scratched the back of his neck, looking down at his drawing. “No.” 

“Well I think you’d find it interesting,” she said, kicking his stool when he didn’t look up at her. 

“Jesus, what the fuck?” Derek asked as he caught himself on the counter. “What is it, Erica?”

“If you’re going to be a dick about it, I won’t fucking tell you,” she said, admiring her nails. When she lifted her eyes to meet his, she smirked. “But believe me, you want to know this.”

“What,” Derek asked, intrigued. 

“What will you give me?” Erica asked.

Derek rolled his eyes. 

“I’m poor, you get my friendship,” Derek grumbled as he pulled at his kneaded eraser, using it to smudge some of his lines. 

“This is something you have to pay for,” she said cryptically as she clicked the mouse, her gaze on the computer screen. 

“No, thank you,” Derek said with a sigh. It was a slow evening, a Wednesday. Derek assumed people must be at church or some shit. There were only two people in the store, both of whom were in two back rooms, making use of the DVD players.

“Give me your credit card,” Erica said, extending her hand out towards Derek. 

“Fuck no,” Derek scoffed. “I’m not falling for that.” 

“I’m serious.”

“So am I!” Derek said. “I don’t want whatever it is.

“Yeah, you do.”

“No, I don’t. What the fuck are you being so secretive about?”

“Ugh, you are no fucking fun. Your lust toy Stiles is doing a live stream and we should watch.” 

“I’m sorry, what?” Derek said, dropping his pencil as he turned towards Erica, his eyes wide. 

“You heard me.”

“I do not lust-- what do you mean Stiles has a stream?”

“I mean he is about to fucking blow a load on screen for however many horny bastards and we should fucking watch, hand me your card.”

Wide-eyed, Derek handed her his wallet as he stood up, walking over to the computer to see what the fuck she was talking about. It had to be some sort of twink look-alike, or something. Derek just about shit a brick, covering his mouth when he saw that it was most definitely Stiles’ picture. Erica shoved Derek out of the way so she could fill everything in, punching in his card information, then clicking ‘join’. 

The feed popped up, and Derek just about fell down. There were four hundred people in the chat with them, and Stiles was sitting there, his chin resting in his hand with a smirk on his face.   
“No just as the title says, still a virgin,” Stiles said, obviously in the middle of a conversation. Derek watched the chat blow up with lewd remarks about wanting to be the one to defile him. He didn’t know how to react as he leaned over Erica, who sat in a stool in front of the computer with her fingers over the keys. Derek smacked her hand when she started typing ‘show us your cock’.

“Don’t,” Derek said. 

“You aren’t any fun,” Erica said, pouting. “I was going to put us in as 'EricanDerek' to see if he noticed. 

“You do and you’re dead,” Derek hissed. 

“Okay, so by popular demand, I’m wearing my cock ring,” Stiles said, lifting an eyebrow. Derek groaned, covering his mouth as he shut his eyes. This was such a bad idea. 

“Turn it off.”

“No fucking way,” Erica said. “This is going to be awesome.” 

“I can’t do this,” Derek said. “He’s eighteen.”

“He’s legal! Congrats, now nut up and shut up.” Derek quieted down, his eyes trained on the screen in front of him. 

“And to uh, get things going faster, I’m already wearing my plug.” Derek swallowed a moan, his hand clenching the counter in front of him as he moved closer to the screen. 

“Damn,” Erica said as Stiles showed it off. “He has a nice ass.”

“Stop it,” Derek said, his eyes not leaving the screen. He was willing himself not to get hard. He didn’t want to have to kick a guy out of one the back rooms. 

“Shutting up,” Erica whispered as Stiles jacked off, moaning as he lay back on the bed with his legs spread. Derek’s resolve quickly dissolved as Stiles took out his plug, revealing his ass, only to turn on the blue vibrator that matched Derek’s own. 

“Shit,” Derek said. Stiles was a camera whore and had been using the toys Derek picked out for him. “Fuck.” It was hotter than Derek thought it would be, he had to admit. It also made him rock hard. He shifted in attempt to hide it from Erica, but there was no way she couldn’t know. She tilted her head as she watched, her arms crossed over her chest. 

“I bet he’d be a ragdoll when you fuck him.”

“I’m not going to fuck him,” Derek said, his voice catching in his throat. Erica snorted, but her eyes didn’t leave the screen as they watched Stiles use the vibrator on himself, moaning loudly. Derek turned the volume down so it wouldn’t be obvious they were watching porn. 

Not that they couldn’t, really. 

Derek jumped out of his skin when the buzzer rang. He looked to Erica, who pointed at him. 

“What?” Derek asked. 

“I’m running register, you are doing the door.” Derek groaned, looking over his shoulder as he walked over awkwardly to the window, readjusting himself as he went. It was a group, which made Derek angry. He didn’t want more people in the store now. He wanted to watch Stiles. He buzzed them all in after checking their IDs, then ran back over to stand behind Erica. 

“Jesus Christ,” Derek almost shouted as he bit down on his knuckles. Stiles had the mid-sized butt plug, and he just about had it in. Derek thought about what he told Stiles, no dildo until the mid-sized plug. His cock throbbed where it was trapped in his jeans. 

“You okay there, big guy?” Erica asked. “You’re breathing kinda heavy.”

“Fuck you,” Derek said as he leaned forward, hovering over Erica. 

“Back up, I don’t want you poking me with your dick,” Erica said, shoving at him. Derek almost came in his pants when Stiles did, ropes of come shooting out from his cock, into the air then onto his chest as he rocked his hips. Derek felt like he was punched in the gut. 

“I mean it, step back, you’re breathing on my neck.”

“Fuck off,” Derek said as he backed away. A cough caught his attention as he realized someone was waiting in line. Derek shoved at Erica, making her get off the stool. “I did the ID, you got the register.” She stuck her tongue out at him as she went to check the customer out. 

Derek’s gaze didn’t leave the screen as Stiles cleaned himself up, his cheeks flushed as he sat in his chair, swinging back and forth as he answered a few questions that popped up in the chat. 

“I’m definitely legal,” Stiles said with a laugh, his fingers playing at his lips, teasing. Derek cleared his throat to keep from groaning as he watched Stiles’ eyes cast over the chat window. “What are my kinks? Well, uh, that’s hard to say since I’ve never done anything with another person.” Derek’s cock ached as it pressed against his jeans, begging to be taken care of as Stiles’ eyes fluttered shut, his eyelashes apparent as he opened them again. 

“My next session? Well, I don’t know. First I need to take a trip to the store and buy something new,” Stiles said with a wink.

-

Derek was on day seven of working in a row, and he was admittedly in a sour mood. It wasn’t often when it happened, the nonstop shifts, but when it did it definitely took a toll on his moods. He was alone at the store, clicking around on the internet during a lull in customers when he decided to go back to the porn site Erica found Stiles on. The stream put a dent in Derek’s paycheck, that much he knew, but that didn’t mean he thought it wasn’t worth it because that would be a lie. It was most certainly worth the drain of Derek’s bank account. 

He thought for sure that Stiles would have shown up the next day to the store, or the day after that, but it was almost five days later and Stiles still hadn’t shown up. There wasn’t any other signs on the website of Stiles doing another stream, or even when he would be doing one again. 

It frustrated Derek in more ways than one. 

He couldn’t remember the last time he jacked off so often, maybe not since high school. He had to rectify the situation, fast. Of course, Stiles had to show up in the store for that to happen. 

-

Derek had a lazy day around his loft on his one day off. He slept in, walked around in his sweatpants, barefoot, without showering as he drew on a giant sketchpad, his hands covered in charcoal after a while. He ordered in Thai, not even bothering to put on a shirt when he answered the door. 

It wasn’t until he heard his phone beep that he realized the day was almost done, with the sun dipping below the horizon. His phone was still by his unmade bed, hidden beneath a pillow case. He had missed texts from Erica, multiple ones. 

‘He’s here,’ the first read. Derek’s stomach sank. It was from over an hour ago. There was no way that Stiles was still there. 

‘Where are you? Get over here,’ the second said. 

The third was a picture message, obviously a stealth shot taken by Erica of Stiles by the dildos. Derek groaned as he ran his fingers through his hair. The picture was from a few minutes ago. Stiles was still there, maybe. Derek looked down at himself, covered in charcoal and wearing his low hanging, baggy sweatpants. 

‘He still there?’ Derek asked as he walked into his closet. He got out his favorite pair of jeans, faded and well worn, then slipped on a plain grey henley, pushing up the sleeves. His phone beeped in his pocket. When he took it out, he scrambled to get his shoes on. The text read: ‘Yeah, asshole. I’m stalling him.’ 

Derek’s apartment was only a two minute drive down the road, and as he pulled up, he saw a blue Jeep next to Erica’s car in the parking lot. It wasn’t until he got out of his car did he realize that he didn’t know what to say, or have a reason for showing up at work on his day off. Derek almost didn’t get out of his car when his phone buzzed again. 

‘He’s leaving,’ it said. Derek sucked in a breath as he looked up to see Stiles walking out of the store empty-handed, his hands shoved into the pockets of his hoodie. When Stiles noticed Derek, he stopped walking, his hand moving up to his neck, his cheeks red as Derek approached. 

“Hey,” Stiles said as Derek stopped in front of him. 

“Hey,” Derek said, his movements mirroring Stiles’. “Didn’t find anything?” Derek asked, motioning to Stiles’ empty hands. 

Stiles shrugged, his bottom lip catching on his teeth as he grinned. 

“Not this time, my favorite employee wasn’t there to answer my questions.”

“What an ass,” Derek said nonchalantly. Stiles laughed, and all Derek could think about was the stream. 

“I was just going to come back tomorrow,” Stiles admitted. Derek sucked in a breath as he looked to the ground. He liked Stiles, he really did, but he wasn’t sure why he was here, standing in front of him on his day off. 

“Are you stalking me?” Stiles asked. 

It was Derek’s turn to laugh as he nodded his head. 

“Erica texted me.”

“I knew she was stalling me,” Stiles said, puffing his chest out, smug. “She told me, you know.” Derek lifted an eyebrow, feigning ignorance. “About the stream.”

“Ah,” Derek said, unsure of what to say. 

“It’s kind of embarrassing,” Stiles said as he ran his fingers over his mouth. “I didn’t think anyone I knew would find it, which is sort of asinine, you know?” 

“I didn’t-- I’m sorry if that was crossing a line--”

“I’m the one who-- well. I don’t think I mentioned you the last time, actually,” Stiles said. 

“You mentioned me?” Derek asked. 

“Yeah, you know, porn store guy, you’ve been the one answering all my questions. A lot of the people who watch want to know about how I picked the toys and I just told them the truth,” Stiles said with a shrug. “That I didn’t pick them out, you did.” 

Derek’s stomach was in knots as he took another step forward. Stiles’s eyes caught his, his chin lifting slightly as if leaning in. Derek licked his lips as Stiles’ eyes closed, their lids heavy as he breathed out. 

“I wasn’t about to buy something without you there,” Stiles said.

“You’re insufferable,” Derek murmured, his head tilting to the side as Stiles brushed his lips against Derek’s. Derek’s lips were dry, chapped, and as Stiles pulled back his lips caught on Stiles’. Derek put a hand on Stiles’ neck as he brought them together once more, his mouth opening, tongue begging entrance to Stiles’. He felt Stiles’ hands on his shirt, gripping it as he opened his mouth for Derek, letting his tongue slide into the warm, wet heat. Stiles moaned against Derek’s lips as he took a step closer. Derek’s other hand rest on Stiles’ waist as their heads moved as the kiss continued. Derek breathed Stiles in, his own eyes closing as Stiles’ hands snaked around his torso, linking his fingers behind Derek’s back. 

“Wow,” Stiles said as the kiss ended, his eyes opening to find Derek staring at him through his glasses. “Can we do that some more?” Stiles asked, the naivety not lost on Derek. 

“Yeah,” Derek said, his voice catching in his throat as he leaned in for another kiss. Stiles pressed his body against Derek this time, his hand slipping down to Derek’s ass, grabbing hold of it. Derek laughed against Stiles’ open mouth. 

“I’ve wanted to do that for a while,” Stiles admitted as his hands roamed higher up Derek’s back. 

“You have no idea how insane you’ve driven me,” Derek said, his lips grazed over Stiles’ cheek, down his neck where he mouthed at his skin, his hands slipping beneath the fabric of Stiles’ shirt, finding the trail of hair that led down past his briefs. Derek’s fingers brushed against it as his mouth found Stiles’ once more. 

“That’s a laugh, you do realize that blue vibrator, like--” Stiles stopped as he ducked his head away from Derek as he covered his face with a hand as he held onto Derek’s shirt with the other. “Scratch that sentence.”

“No, what?” Derek asked, almost sure of what Stiles was about to say. “You can tell me.”

“It’s embarrassing,” Stiles admitted. 

“Doubtful,” Derek said with a shrug as he ran a thumb across Stiles’ cheek. “You don’t have to tell me anything you don’t want to.” 

“Well, I mean, you know how you have the same one?” Stiles asked. Derek nodded his head, his cock stirring in his jeans at Stiles’ explanation. “I’ve thought about you each time I use it. Well, more so than with everything else.” 

“Oh, Jesus Christ,” Derek said as he sought out Stiles’ lips once more, mouthing at him as he gave in to his desire for him. Derek’s willpower totally crumbled around him as Stiles bit his lip, pulling on it as Derek ended the kiss. With heavy-lidded eyes, Derek let out a low moan as Stiles kissed him chastely. 

“I can’t believe you’re kissing me. Talk about a wet dream come true.” Derek snorted, his eyes shutting as he smiled against Stiles’ lips. His hands found Stiles’ as he brought Stiles closer to their cars so that they weren’t standing in the middle of the parking lot. 

“You aren’t so far from that yourself,” Derek said as Stiles leaned against his Jeep. His lips were red, swollen from kissing. Derek wanted to see what his mouth looked like after other activities, too. Stiles rolled his eyes, though. 

“Yeah, okay,” he said, self-deprecating. 

“Hey,” Derek said, bringing Stiles’ attention back to him instead of whatever internal issues he had with himself. “Let’s get out of here.”

“What do you have in mind,” Stiles asked. Derek knew Stiles lived at his parents’ house, that if they were to be alone, they had to go to Derek’s loft. He didn’t want to freak Stiles out, think he had to put out immediately, or feel any pressure. Derek was good with going slowly, even if his body’s reaction wished otherwise. 

“We could grab a bite to eat,” Derek suggested, even though he had uneaten Thai food waiting at his loft. Thai tasted good reheated, anyways. “Or we could head to mine--”

“I pick door number two,” Stiles said without thinking. Derek leaned in, kissing him once more. 

“Follow me, then.”


	4. Chapter 4

**Notes for the Chapter:**

> I feel like I should tag this fic as a plot what plot because let's be real here.  
> You guys are the best. Thanks for reading!

Stiles drummed his fingers against the steering wheel of his Jeep as he followed Derek’s Camaro down the road. It was a short ride, shorter than Stiles was prepared for, if he was being completely honest with himself. He thought he had more time to prepare, or something. But no, Derek lived practically right around the corner from the store. He parked beside Derek, waiting a second before getting out of his car. 

He was nervous. Sure, he just made out with Derek in the parking lot of the store, but that didn’t mean he was certain what he was doing. It hadn’t been his first kiss or anything, that belonged to Heather when he was sixteen. After that, though, there hadn’t been much. Stiles held his breath as he joined Derek by the door to the building, giving him a small, awkward smile before they ascended a flight of stairs. 

“I wasn’t expecting company,” Derek told him as they walked up another flight, then another. Stiles, mesmerized by Derek’s ass as he walked up the steps ahead of him, only shrugged his shoulders in response. 

“My room is a mess,” he lied. He was OCD about his room, especially his bed. Derek seemed unfazed by Stiles’ comment as they stopped in front of a large sliding warehouse door. 

“Cool,” Stiles said as Derek opened it, showing him a loft. It was apparent just how different they were. Stiles was still in high school, and here Derek was with a loft and a Camaro he probably bought for himself with two jobs and-- “Holy crap is that something you drew?” Stiles asked as he stepped into the loft, looking at the giant sketchbook that lay on the floor of the living area with charcoal surrounding it. 

“Yeah, that was earlier--” 

“Holy shit,” Stiles said as he bent over, practically kneeling by it. It was obviously a body, a collarbone, with a bruise, a hickey at the base, along with teeth marks. The shading made everything deeper, more meaningful. Stiles looked up at Derek as he licked his lips, his chest constricting when he saw how Derek looked at him, his pupils blown. 

“Come here,” Derek said, his voice soft, welcoming. 

Stiles stood up, slipping into Derek’s arms easily, his hands resting on Derek’s hips as they kissed. Stiles decided he could kiss Derek all damned day, it was that addicting. Stiles’ anxiety about how inexperienced he was rushed out of his body as Derek cradled Stiles’ head in his hands, tilting Stiles’ head to the side, his mouth guiding Stiles’ as they kissed, their tongues tangling in their mouths. Stiles moaned, his eyes closing as Derek’s thumbs brushed his ears, his fingers holding the nape of his neck. 

Stiles throbbed between his legs as all the blood in his body flowed south, he couldn’t think straight as Derek walked him towards what Stiles assumed would be the couch. Stiles fell onto it, his knees bending as he sat. Derek, with one knee on the couch, bent over as Stiles turned his face away. Derek’s stubbled face rubbed against Stiles’ exposed neck, sending a shudder down his spine. Derek’s hand was against Stiles’ chest as they continued kissing, holding him against the back of the couch as he sat next to Stiles. Derek’s knee was bent, tucking beneath him as he faced Stiles. Not knowing what to do with his hands, Stiles placed one on Derek’s thigh, his nails scratching against the fabric as the other gripped Derek’s shirt with a fist. 

“Eager,” Derek said as his lips brushed against Stiles’ chin. Stiles’ lips found Derek’s once more, not wanting to stop. His hand slid higher on Derek’s thigh, his fingers teasing the inseam of his jeans. Stiles’ dick jumped in his jeans as Derek let out a low groan. Stiles did the movement again, this time moving higher up Derek’s thigh, almost to his crotch. 

Derek grabbed ahold of Stiles’ wrist, stilling his ascent. Stiles licked his lips as he looked Derek in the eye, his eyes flicking to Derek’s reddened, swollen lips. Derek guided Stiles’ hand away from his crotch as he kissed Stiles again. 

Stiles surged forward, his lips locking against Derek’s once more as he pushed Derek against the couch, his head against the armrest. Stiles lay down on top of him, a leg slipping between Derek's, his other pressed against the couch as he moved against him. Derek moaned beneath him, his hands holding on to Stiles’ waist as Stiles rutted against him. Stiles moaned as he sought friction, his erection needing more than the rub of fabric. 

“Hey,” Derek said, his voice just as soft as before, albeit hoarser as they stopped kissing. “There’s no rush.” Stiles’ cock throbbing between his legs begged to differ, but as Derek pressed his lips against Stiles’ chastely, Stiles melted in Derek’s arms. Stiles nodded his head, kissing Derek’s stubbled chin, then mouthed at his neck. Derek gasped as he tilted his head upward, exposing his neck for Stiles as his hands slipped beneath the fabric of Stiles’ shirt once more, then slid down to his ass. Stiles grunted as he rolled his hips, rutting against Derek’s leg shamelessly. Derek, too, moved against Stiles. He could feel Derek’s erection, could see the bulge in his jeans. Stiles brushed his hand over it again, sliding his hand underneath Derek’s shirt, then back down again. 

Derek was responsive beneath him, his own hands gripping Stiles’ ass, pressing a finger between his cheeks. Stiles moaned against Derek’s neck, his brow drawn together. Derek urged him not to touch his crotch, but there he was with his hands on Stiles’ ass. Stiles didn’t know the rules, didn’t know what Derek wanted or what he should do. He slowed his movements, his hand stilling over Derek’s taut stomach. Stiles swallowed as he rested his head on Derek’s shoulder, his eyes searching as he licked his lips. 

“I don’t know what I’m doing,” Stiles admitted. Derek’s grip on him loosened immeasurably, one sliding up to Stiles’ lower back as the other rubbed at his face, sliding his glasses up as he covered his eyes. 

“I know you don’t,” Derek said, pained. Stiles didn’t want to stop, didn’t want Derek to think he didn’t want to continue because he most certainly did. 

“What do you want me to do?” Stiles asked, hoping that helped. Derek had his free leg propped up, his knee bent and spread outward as he craned his neck to attempt to look Stiles in the eye. Stiles pushed up off of Derek’s chest, using his hand on Derek’s stomach to hold himself up. 

“That depends,” Derek said as he cleared his throat, placing his free hand on his stomach, below Stiles’ own hand. “On what _you_ want.” 

“I want to continue what we were just doing,” Stiles said with a laugh. Derek gave him a smile as Stiles got lost in his eyes that seemed to shift color. 

“We can do that,” Derek said, his face leaning forward, his eyes closing once more. Stiles let himself fall back against Derek, his arm wrapping around him as he lay completely on top of him as they kissed once more. The desperation that was there before subsided, leaving them breathless yet Stiles no longer felt as though he was about to come in his jeans. 

After awhile, though, Stiles began to move against him once more, unable to help himself. He couldn’t believe after the weeks of going into the store, of practically ogling Derek, that he had him beneath his body right now. Stiles’ hands roamed Derek’s torso, sliding his shirt up his chest, his fingers ghosting over a nipple. Stiles gasped when he felt the barbell, tiny, pierced through Derek’s nipple. Distracting him from kissing Derek, Stiles shoved Derek’s shirt up further to look, his thumb grazing over it before he bent his head, licking it before mouthing over it completely. Derek arched his back beneath Stiles, his hand holding on to Stiles’ head, keeping him there, teasing at Derek’s pierced nipple as his legs spread. Arched over Derek, Stiles palmed at himself through his jeans as he felt the intensity building once more.

Derek gripped Stiles’ chin, guiding him back up to his mouth so they could kiss, their mouths crashing together, the both of them groaning. As the kiss ended, Stiles sat up, his hand still on his crotch as he watched Derek discard his shirt, tossing it to the floor. Stiles gawked at Derek’s physique, at his muscled stomach and torso, at his pecs, at the piercing and tattoos that were finally fully exposed to him. Stiles rocked his hips against Derek’s thigh as he bit his lower lip, his eyelids heavy. 

Derek’s hands slid up Stiles’ body slowly, a hand gripping Stiles’ shirt, urging him forward. Stiles moved his legs, straddling Derek’s stomach instead of his leg as he held onto the armrest on either side of Derek’s head. 

“You okay with this?” Derek asked. Stiles nodded as Derek palmed Stiles through his jeans, his other hand roaming up Stiles’ torso. “Take your shirt off.” Stiles did as Derek requested, throwing it to the floor beside Derek’s shirt, his hands returning to the armrest as Derek's hands grazed over Stiles’ bare torso, pale in comparison to Derek’s form. Derek’s mouth on Stiles’ nipple shouldn’t have made him moan like he did, but he maintained that he couldn’t help it, what with it being his first time. Stiles shuddered as Derek’s fingers outlined his erection, stroking him through the fabric of his jeans. 

“Oh, god,” Stiles said as Derek’s teeth raked over his nipple. He wasn’t going to last long with Derek touching him he needed-- 

“I need something, I’m not gonna last,” he gasped as Derek’s grip on him tightened. Stiles looked down to find Derek looking up at him, his mouth hovering over Stiles’ nipple, his bottom lip almost caught on it. 

“Do you?” Derek asked, seriously. Stiles bit his lip as he thought about it, really thought about it. He nodded his head as Derek licked up Stiles’ chest, hooking a hand around his neck to bring Stiles’ mouth closer to his own. In a swift movement that Stiles wasn’t sure he completely comprehended, Derek flipped Stiles onto his back on the couch as he continued to kiss him. Stiles tugged at Derek’s belt loops, keeping him on top of him despite Derek’s best efforts to get off the couch. 

“I’ll be right back,” Derek said, his hand on Stiles’ throat as he kissed him with closed lips. Stiles let Derek get off the couch, his hands falling to his own stomach as he watched Derek walk into another room. It looked to be his closet, Stiles thought as he pushed himself up by his elbows. 

He watched Derek walk back towards him, his stomach in knots when he saw that Derek had a cock ring with him, black with flat silver studs on it. One of the ones that Stiles made fun of at the store as being too flashy. It wouldn’t keep him from coming, but it would certainly keep him hard longer. 

Stiles’ face reddened as Derek knelt in front of the couch, holding the ring in his hand as he bent over for a kiss. Stiles relaxed once more as Derek placed a hand on his chest, lowering him back down onto the couch. 

“Do you want to put it on?” Derek asked, his hand resting over Stiles’ lower stomach, his fingers grazing over the trail of hair that led down beneath Stiles’ jeans. His boxer briefs peaked out from his jeans from how he moved, letting the jeans ride low on his hips. Stiles spread his legs instinctively as Derek’s hand cupped his erection. 

“You can,” Stiles said, his voice shaky as Derek rubbed against his straining cock. He rolled his hips, seeking more friction as Derek unzipped his jeans. Stiles panted open-mouthed as he watched Derek free his cock, his hands warm on him. Stiles zoned out as he watched Derek snap the cock ring in place, his hands roaming Stiles’ body as he bent over, taking Stiles’ cock into his mouth. Stiles gasped, gripping onto the couch cushions at the feeling of Derek’s mouth wrapped around his cock. Stiles’ chest heaved at the warmth, the wetness as Derek’s tongue teased at the head of his cock. Derek moaned as he took Stiles all the way into his mouth, sinking down so that Derek’s nosed brushed against the patch of hair at the base of Stiles’ cock. Stiles’ back arched as Derek sucked, his fingers grabbing hold of Derek’s hair as he held him down. 

“Fuck,” Stiles said, his stomach contracting as his body shook. Derek pulled off, gasping for air as he knelt back on his heels, wiping at his mouth. 

Before continuing, Derek leaned over, kissing Stiles again. Stiles could taste himself on Derek’s lips, a hint of saltiness that wasn’t there before. His tongue searched Derek’s mouth further, keeping him close as Derek began to slowly stroke Stiles’ cock, his thumb teasing his head. 

“Want me to jack you off?” Derek asked. Stiles nodded his head as Derek grinned against his lips. “Wait here.” 

While Derek disappeared again, Stiles rid himself of his jeans and briefs completely, returning to the position he was just in. Derek lifted an eyebrow at him but said nothing else as he tossed one of the throw pillows to the floor for his knees as he knelt. He had a half-empty bottle of SILK lube that he set down next to to him. Stiles watched him pump it twice, then spread it over the palms of his hands, warming it as he looked over Stiles’ body. 

He felt exposed, under scrutiny, as Derek wrapped a lubed hand around his cock. The slide was smoother, much smoother as Stiles fucked up into Derek’s lose grip. 

“Let me,” Derek said, his voice calming. Stiles stilled his movements, holding on to the couch cushions once more as Derek stroked his cock, twisting his wrist as he did so. He started with one hand, then moved to two, his fingers moving in opposite directions as he jacked him off. Stiles watched with his mouth open as Derek thumbed at his slit. 

“You’re so receptive,” Derek commented. His face was impassive as he concentrated on working Stiles into a frenzy. “I’d like to see what would happen if I really got to open you up.”

“Oh, god,” Stiles said with a moan, his eyes shutting at Derek’s words. The pressure he felt because of the cock ring was immense. “Fuck, don’t say that if you aren’t going to.” 

“Only if you want me to,” Derek said, his voice low as he continued to jack Stiles off. Stiles grunted, a hand holding on to Derek’s bicep as his stomach spasmed, coming in Derek’s hands. As his body shook with it, Stiles couldn’t help but laugh. He still hadn’t lasted long, despite the ring, his hard on remaining. 

Derek stood up before Stiles could say anything, he felt like his entire body buzzed beneath the surface as he reached for his briefs, feeling weird staying naked while Derek returned still wearing jeans. 

“So, about food?” Derek asked. 

Stiles looked to Derek’s crotch, which was about eye level, then caught Derek’s gaze. 

“What about you?” Stiles asked. “Do you need me to--”

“No,” Derek said, helping Stiles to his feet. “You don’t need to.” Stiles brow furrowed, clearly confused. 

“Don’t you want me to?” Stiles asked as Derek kissed him. 

“Yeah,” Derek said as he wrapped his arms around Stiles. “I do, but you don’t have to yet.”

“What if I wanted to?” Stiles asked, lifting an eyebrow. “Like, really, really wanted to.”

“Is that what you want?” Derek asked. Stiles nodded his head against Derek’s lips, not wanting to stop kissing him again. “What do you want to do?” 

“I want to taste you, to put you in my mouth,” Stiles said as he slid his hand over Derek’s crotch, rubbing against his jeans. Derek hissed as Stiles tugged him back towards the couch. Stiles sat back down, linking his fingers in Derek’s belt loops to pull him forward a few more steps. Stiles didn’t show how nervous he was as he grabbed at Derek’s erection through the fabric of his jeans, looking up at him through heavy-lidded eyes. 

He came so many times thinking about Derek’s cock, and now that he had it right in front of him he couldn’t help but feel a little bit shy. He felt his cheeks heating up as he undid Derek’s zipper, the button on his jeans. Derek shoved the jeans down his thighs as Stiles mouthed at Derek’s briefs, outlining Derek’s cock with his mouth, sliding his tongue against the cotton fabric.   
Derek put his hand on the back of Stiles’ head as he hooked his fingers around the waist band of Derek’s dark briefs, pulling them down to reveal the head of Derek’s cock. Stiles’ tongue lapped at it as he breathed against it as he slowly freed the length of him. Stiles tried not to feel intimidated as Derek thumbed at his ear affectionately. 

Stiles would be lying if he said that Derek’s cock was normal-sized. Normal was like, six or seven inches, like his. His cock was normal length and girth. Derek’s was most certainly not. Derek’s was like the monster dildo that he said he couldn’t take, that he had to work up to. Stiles licked up Derek’s length slowly, taking it in his hand as he sucked at the tip, opening his mouth to take it in. Meanwhile, Stiles jacked Derek’s cock, his mouth open as he ran it along the length with his eyes looking upwards. 

He thought about the store, about Derek’s words of warning about the dildo, about working up to it, needing to make sure he was ready. Stiles’ ears were red at the thought of it as he closed his eyes, taking Derek’s cock into his mouth. It spread his lips wide as he kept his hand wrapped around the base of it, taking it as far into his mouth as he could. 

His own erection, things to the ring, throbbed between his legs. He could feel the pressure as it kept him hard. He palmed himself as he looked up at Derek, his mouth full. 

“You’re doing good,” Derek encouraged him. “That feels great, yeah,” Derek moaned as he slowly rocked his hips against Stiles’ mouth. Stiles pressed a hand against Derek’s lower stomach, noting how he kept himself trimmed, groomed, as opposed to Stiles whose pubic hair seemed untamed next to Derek’s. Stiles dragged his fingers across the short, coarse hairs as he licked up Derek’s length once more. 

“Do you want to jack me off?” Derek asked. 

Stiles shook his head, his lips lightly rubbing over Derek’s cock as he protested. He wanted to make Derek come with his mouth. Stiles was determined to. He took Derek into his mouth once more, his head bobbing back and forth as he slid the bottom of his tongue out, tasting the underside of Derek’s cock. Derek closed his eyes as he held on to Stiles’ head, guiding him down his cock. Stiles placed his hands on Derek’s thighs as he took as much as he could. When he hit the back of Stiles’ throat, Stiles gagged, coughing as he pulled back, his eyes watering as he gasped for hair. 

Derek’s thumb was there, near his mouth, wiping at a trail of spilt that connected his cock to Stiles’ lips, ending it before he pressed his thumb against Stiles’ mouth. Stiles took the digit into his mouth, sucking on it as he looked up at Derek. Derek’s cock hung heavy between his legs, spit slick from Stiles’ mouth. As Stiles sucked on Derek’s thumb, he took Derek’s cock in his hand, slowly jacking him off. 

“Yeah, just like that,” Derek said, moving against Stiles’ fist. Stiles bent over, reaching for the lube. He pumped it once, taking Derek’s cock in his slicked hand this time for easier movement. Derek groaned as he pressed his thumb down against Stiles’ tongue. Stiles sucked at it more, his tongue swirling around it as he watched Derek fuck his fist. Derek’s pace quickened, and as he threw his head back, Stiles felt his hot, sticky come splatter against his bare chest. Stiles moaned against Derek’s thumb as he pulled it out of his mouth. 

“Was that-- was I okay?” Stiles asked, his eyes wide as Derek helped Stiles to his feet. 

“Yes,” Derek said as he kissed Stiles. His lips felt numb as Derek cupped Stiles’ face with his hands. Derek took Stiles’ cock in his hands, snapping the cock ring off of him before jacking him off. Oversensitized, Stiles grabbed onto Derek, his toes curling as his second orgagism rushed through him. 

“Fuck, fuck,” Stiles said as he watched Derek lick his hand, cleaning up the mess. Stiles couldn’t help but rest his head on Derek’s shoulder as Derek pulled up Stiles’ briefs, covering him up from where they were shoved down his thighs, just out of the way.

“Let’s clean up. I have Thai we can reheat.” 

“Okay,” Stiles said, realizing how thirsty he was. Derek grabbed a damp paper towel, handing it to Stiles so he could clean up. Stiles knew his cheeks were still flushed, but as he walked into the bathroom and looked in the mirror, he was shocked to see how debauched he looked. His mouth was red, he had stubble burn on his neck, and he had never seen his lips so puffy before. He splashed cold water on his face, but it didn’t help much. He got dressed, then emerged to find a glass of ice water waiting for him. He downed it, then refilled it as Derek heated up the Thai food in a skillet on the stove. 

“Pick out a movie,” Derek said, bringing Stiles out of his revelry. He had been watching Derek’s back muscles move, his eyes lingering on the sole tattoo on his back: a triskelion. Stiles smiled to himself. Derek wasn’t going to kick him out after messing around. He wanted him to stay, to eat dinner with him, to watch a movie. Stiles took his time picking out the movie that they would watch on the couch, wrapped in each other’s arms.


	5. Chapter 5

**Notes for the Chapter:**

> i think instead of plot what plot i am calling this fic "sexcapades"
> 
> also, foreverblue-navy made this [awesome cover](http://foreverblue-navy.tumblr.com/post/80838681640/this-bookcover-for-my-friend-beth-today-is-her) for the fic! I think it fits the fic perfectly :)

The credits rolled in the background, the music waking Derek up from where he fell asleep watching a movie. He got home from the gallery, late, then crashed after pulling a double. Derek lay there, staring at the TV blankly as his phone buzzed from on the coffee table. He grunted as he sat up, rubbing at one eye as he picked it up, unlocking the screen to find a text from Stiles. Derek smirked as he stood up, heading towards his bathroom to brush his teeth before calling it a night. 

He stripped down to his briefs before he crawled into bed, lighting up the dark room with his phone as he began typing back a response. Stiles exchanged numbers with him before leaving a few nights ago, but he hadn’t heard from him until now. 

‘Hey, you up?’ Stiles’ text read. It was simple, really, but it made Derek smile nonetheless. 

‘Fell asleep on the couch, in bed now,’ Derek responded. Almost immediately, he got a reply. 

‘If I was there you wouldn’t have fallen asleep.’

‘I disagree. That would have been more incentive to.’

‘Are you a cuddler, Derek?’ Stiles’ text read. Derek laughed as he looked up at the ceiling. This kid was going to fuck him up royally. 

‘Not usually.’ 

‘That’s unacceptable. I want a refund.’ Derek groaned as he thought about Stiles the other day, so ready to try anything, his noises and how reactive he was to every touch. How his mouth looked with Derek’s cock in it. 

Derek hadn’t intended for things to get that heavy so fast. He wanted to make out, of course, maybe something a little more, but he definitely didn’t think about how Stiles would react to him. In the middle of them making out, when Stiles put his hand over Derek’s crotch, he panicked. He knew how inexperienced Stiles was, despite the amateur porn stream, and tried to deflect by putting more attention on Stiles’ pleasure rather than his own. 

He knew how intimidating his cock was; it wasn’t like he didn’t know. Size does matter, and when someone is on the ‘how big is too big?’ side of large things weren’t as easy as ‘just put it in.’ No, Derek couldn’t ever just go at it, and when Stiles put his mouth around him, Derek saw how intimidated he was. 

‘No refunds available, sorry,’ Derek typed back, unsure of what they were really talking about. He wasn’t good with coy, or flirting. He was good at sex. Derek worried at his bottom lip as he thought about Stiles staying afterward, about them curling up and watching _Thor 2_ together before he headed home. That wasn’t something he did normally, but then again, Derek hadn’t actually dated in a few years. 

He was bi and had his fair share of twosomes, threesomes, and moresomes, but he had been denying himself the personal level of intimacy by preferring one night stands to having actual relationships. After Jennifer, well... and Kate, Derek didn’t consider himself ready. He liked his solitude, partying with his friends. 

‘You’ll have to make it up to me, I guess.’ 

Well that got Derek’s attention in more ways than one. Stiles’ text woke him up from his hazy, almost-asleep state. When his phone buzzed again, Derek groaned without even looking. He had a feeling he knew what it would say. ‘Want to see what I did today?’ 

Derek was wrong, he wasn’t prepared for that text. His dick stirred between his legs, reacting to Stiles’ text. His dick betrayed him, basically. He palmed himself through the fabric of his briefs, his fingers outlining the bulge. 

‘Show me,’ Derek sent back as he kicked the sheets off of him, then slipped his briefs down his thighs. He thought about staying in bed with the lights off, but as his phone buzzed again, he got out of bed and turned on the light; just after midnight, so it was still early. Derek walked into the living room, where the lube still sat on the coffee table from the other day. He stroked himself, feeling himself harden beneath his hand as he made his way back into his room. He set the lube down on his bedside table, then checked his phone: it was a picture of Stiles. He, surprisingly, had clothes on, just a pair of sweats, but still. Derek half expected it to be Stiles with some sort of toy, perhaps his plug in or something, but what the picture was, well. Stiles apparently had been doing yoga, because his head was practically in his own lap. 

The picture was PG at best, but apparently Derek’s cock thought differently. He grunted, his hand sliding up and down his length as he attempted to type back a response. 

‘Been practicing?’ 

‘Yoga is really relaxing,’ Stiles texted back seconds later. Derek imagined Stiles in a downward dog position, the whatever animal it was when the back was concaved, the ass sticking up. Cow? Derek couldn’t remember the last time he did yoga; yoga was Jennifer’s thing. But he remembered how the poses looked. 

Derek’s erection flagged. It was probably for the best, considering Stiles wasn’t sending him what would be generally considered dirty texts. They were tame, conversational. 

‘What are you doing?’ Stiles asked after Derek didn’t respond. 

‘Nothing.’

‘Is that code for jacking off to thoughts of me in compromising yoga positions? Because that was the plan.’ That little shit. Derek laughed as he sat on the bed. 

‘You had me thinking you actually wanted to talk about yoga.’ 

‘Fuck no,’ Stiles said. ‘I’m jacking off actually. Using the voice function to text.’ Holy shit. This kid had no shame, none at all. Derek’s thumb hovered over the call button. He’d rather talk than text. With one hand on his dick and the other holding his phone against his ear, he waited for Stiles to pick up. When he did, Stiles laughed. 

“Hey there,” he said, his breath catching in his throat. He was definitely jacking off. Derek pumped lube into his hand, then stroked his cock. 

“Hey,” Derek said, holding back a groan. 

“Fuck, are you jacking off too? I was hoping-- I didn’t know if you would be.” 

“I was just starting,” Derek admitted. “I wasn’t sure if you were flirting or not.” 

“We can’t all be walking sex gods who don’t need to flirt to get laid,” Stiles said. Derek snorted. He was no sex god, but Stiles seemed to realize it didn’t take much for Derek to pick someone up. “I’m new to this.”

“I know,” Derek said, exhaling as he ran his thumb over the head of his cock. 

“God, I want my mouth on you again,” Stiles said. Derek could hear the distinct sound of Stiles’ hand moving against his cock, his breathing stilted. 

“I’d like that,” Derek said as he let out a moan. He fisted his cock in his hand, picking up his pace to the sound of Stiles’ ministrations.

“This isn’t weird, is it?” Stiles asked, his breath hitching in his throat. “I mean I was thinking about you, now we’re talking and I--” Stiles shouted, groaning through his climax. He shifted the phone around, and Derek couldn’t help but stand up and walk into his closet, finding his fleshlight. He wanted Stiles’ mouth, and it was all his fault for mentioning it. 

“It’s not weird,” Derek said. “Can you--” Derek hesitated before asking, but he wanted to see. “Show me.”

“Show you-- what? My come all over my chest?” Stiles asked, and Derek groaned at the thought of it as he slid the fleshlight down over his cock. He cradled the phone between his shoulder and cheek so he could use both hands as he sat down on the bed, fucking up into it. 

“Yeah, show me,” Derek said as he hit speaker. Fuck it, he lived alone, Stiles knew what he was doing. 

“Shit, are you-- what are you using right now?” Stiles asked, his voice getting higher with each word. 

“Fleshlight,” Derek grunted. “Thinking of your mouth.” Derek lost it as Stiles whimpered over the line. His phone buzzed, letting him know that he received a picture message. “Shit, Stiles,” Derek hissed as he caught a glimpse of Stiles’ bare chest, covered in ropes of his own come. It was a downward angle, and it made Derek want to lick up the line of hair that lead to his navel. There was only a hint of Stiles’ cock, the picture cutting off at the line of pubic hair. 

“You’re gonna make me hard again,” Stiles said. 

Derek pulled the fleshlight off, because he didn’t want to come in it, as soon as he did he jacked off, coming on his own chest. He panted, his chest heaving as he lay back on the bed. 

“Was it good for you?” Stiles joked. 

“Yeah,” Derek said, his voice cracking. 

“Good,” Stiles whispered. “Hey do you think--”

“Do you want to meet tomorrow?” Derek asked, clearing his throat. He hadn’t meant to cut Stiles off. He sat up, grabbing tissues from the bedside table to clean up with, though he preferred wet wipes, but those were in the bathroom and he didn’t really feel like moving again. 

“Yeah,” Stiles said. Derek could tell Stiles grinned by the sound of his voice. Derek ran his hand over his face, closing his eyes. 

“I get off work at seven tomorrow.” 

“Perfect, meet at your place?” Stiles asked. Damn, that was forward. Derek chuckled as he shook his head. He wasn’t going to deny Stiles. 

“Sounds great. I’ll see you then.”

-

Derek deemed the next day the longest day in existence. He kept himself occupied in the day’s lull in customers by playing QuizUp. He was at level 30 in Paintings, thanks to his Art History minor, and level 45 on Quentin Tarantino. He kept being asked for rematches, though. Sore losers were sore losers. 

No one else was on the schedule, so he was alone in the store when the door buzzed. He groaned because he had to forfeit his game to check their ID. His face lit up, though, because it was Stiles who was at the window with a smirk on his face. It was just after three, so school just ended not even thirty minutes ago. Stiles came to the store as soon as he got out. 

“ID,” Derek said. Stiles rolled his eyes, his shoulders falling. 

“Come on,” he complained. 

“Nope,” Derek said, looking upwards. Stiles mimicked him, his mouth forming an ‘O’ when he spotted the camera. He slid his ID towards Derek, who gave a half-assed look at it before handing it back, then buzzing him in. When Stiles walked in, he whistled. 

“You look busy,” Stiles said as he leaned against the counter, putting his head in his hand as his elbow rested on the countertop. 

“Very,” Derek said as he leaned on the counter, his arms crossed as they lay on the counter. Stiles stared at his tattoos again, his mouth hanging slightly open. “Can I help you with something?” Derek asked, teasing. Stiles’ eyes met his, the iris all but gone from them as his pupils were blown wide with want. The look of him sent all the blood rushing from Derek’s head. 

“Yeah, you can,” Stiles said as he licked his bottom lip, then bit at it. “I’ve got a date tonight, and I was wondering if you had any suggestions on how to prepare for that.” Derek swallowed as he looked down at the counter, his eyes closing as he willed himself to keep it together. 

“What kind of preparation?” Derek asked. 

“Well, I already know about the whole cleanliness aspect, thanks to you,” Stiles said, his finger tracing an invisibly pattern in the counter as he avoided Derek’s gaze. Derek’s entire body throbbed as he thought about his mouth on Stiles. “But what I was wondering about is, well, personal preference.”

“Personal preference to what?” Derek asked, his voice hoarse. 

“Body hair,” Stiles said, leaning in closer. “See, I noticed that the guy I’m seeing,” god if that didn’t make Derek’s dick throb more, the thought of Stiles saying they were together. “He’s groomed, you know? Trimmed and manscaped and--”

“Stiles,” Derek said, knowing Stiles was about to ramble. Stiles stopped, his cheeks reddening. “You don’t have to pretend to ask me like this is my job. You can ask me as me.” 

“It’s just, I don’t want to fuck up,” Stiles said as he cleared his throat. 

“You can do what you want with your body hair,” Derek said. “I prefer being closely trimmed for myself because that’s how I like it. You don’t have to do anything you don’t want to.” Stiles nodded his head, exhaling a breath Derek hadn’t realized he had been holding. “There is nothing to stress about, okay?” Derek said as he put his hand over Stiles’. 

“Except the size of your dick, you mean,” Stiles said with a smirk. Derek laughed, shaking his head as his thumb caressed the back of Stiles’ hand. 

“We’ll work you up to it,” Derek said, his voice low. Stiles looked into his eyes with the same heavy gaze as before as he nodded his head slowly. 

“Okay,” Stiles said. “I’d like that.” 

“Good,” Derek said leaning over the counter. The kiss was short but made him smile. “Don’t worry about tonight.” 

“Okay,” Stiles said, chasing Derek’s lips with his own, his eyes closed. 

“Maybe do some yoga first,” Derek teased. “Limber up.”

“Oh, I will,” Stiles said. “Believe me, I will.” 

-

They forewent the couch entirely by heading straight into Derek’s bedroom. Derek had Stiles pinned to the bed, his hands holding Stiles’ wrists above his head as they made out. Stiles moved against him, his legs hooked around Derek’s waist. Stiles mouthed at Derek’s neck as Derek ground his hips into Stiles’. They were taking their time, working up to stripping down, getting to know each other’s mouths and bodies. Derek was aching to get Stiles naked beneath him, but he knew there wasn’t really any rush. It was a Friday night, and Stiles had no curfew. 

Derek stilled as he thought about how Stiles could have one, that he was still in high school. Young, impressionable, and Derek could be seen as taking advantage of him. Stiles’ brow drew down as he moved his hands from over his head, cupping Derek’s face as he smoothed out the lines across Derek’s forehead. 

“Where’d you just go?” Stiles asked. 

“I’m twenty-seven,” Derek said as he attempted to sit up. Stiles’ thighs tightened, stopping him from moving. 

“Good for you,” Stiles said as he raked his nails over Derek’s stubble. “Are you freaking out because I’m in high school?”

“Yeah,” Derek admitted. 

“If you say I don’t know what I want--”

“I don’t doubt that you think you know what you want,” Derek said as he wrenched himself from Stiles’ grip. 

“What is this really about?” Stiles asked. “Earlier you were-- you said I didn’t have to worry.” 

“You don’t,” Derek said as he rubbed at his face as he sat on his bed, shirtless. 

“You’re freaking me out,” Stiles pointed out. “We were making out and getting ready to fuck around--”

“Is that what you want, to fuck around?” Derek asked. “I mean it, is that what you want from this?” 

“Uh, well. I don’t know what’s on the table, honestly,” Stiles said. “Experimenting with my sexuality is A+, and fooling around with you is like a wet dream come true to be fucking honest. If not you, then someone else?” That made Derek’s stomach lurch. The thought of Stiles going to one of the clubs around town, or even to one of the sex parties Derek knew happened, made him groan.

“Not someone else,” Derek said, sighing. “And experimenting is the best part,” he tried to smile. “I just don’t want you to regret anything.”

“I’ve no complaints so far,” Stiles said. “Except that I’d rather be naked right now.” He reached out for Derek, scooting closer to him until he straddled Derek, sitting in his lap as he kissed him again. “Do you want me?” Stiles asked. Derek nodded his head as his hands slid up Stiles’ back

“So much it scares me,” Derek admitted against Stiles’ lips. Stiles backed up enough that he could look Derek in the eyes, searching for something. Derek didn’t do relationships, but the thought of being casual with Stiles made him uneasy. It wasn’t just sex, and they hadn’t even had it yet. 

“Ditto,” Stiles said, sighing as he looked around the room. “Do you have a sex swing?” Stiles asked as his fingers carded through Derek’s hair. Derek lifted an eyebrow at the change of topic, but was glad of the distraction. 

“Maybe,” Derek said as he gripped Stiles’ ass with both hands. Stiles moved against him, smirking as he looked to the ceiling, finding where the swing could hang from. Derek knew he found it when Stiles pointed. 

“There,” he said. “You do, don’t you?” Derek grunted as he buried his face against Stiles’ neck. He was too perceptive. 

“Yes,” Derek murmured against Stiles’ skin as he mouthed at his neck languidly. “But you aren’t ready.” 

“I know,” Stiles whispered. “But I’d like to, you know, be fucked in one.” Derek groaned as his hand slipped beneath the waist of Stiles’ jeans, his fingers sliding between Stiles’ asscheeks. Stiles moaned against him, hands on Derek’s bare back. “Can we, like, make out more, or something? Because I’m dying here.” 

“You’re not dying,” Derek said as he flipped Stiles back onto the bed. “Yet.” 

Stiles moaned as Derek kissed him. He shoved Stiles’ shirt up his torso, his mouth finding a nipple. As Stiles rid himself of his shirt, his arms over his head, Derek took advantage and licked up the underside of Stiles’ arm, burying his face against him, breathing the heady scent of him in. 

“Not that I’m not okay with you, like smelling me, because that is actually hot as fuck, but I’d either like another go at blowing you, or for you to like--” Derek kissed Stiles again for being bossy and vocal about what he wanted. 

“Do you want to learn how to take me?” Derek asked. Stiles nodded his head eagerly as he slid his hands up Derek’s biceps. Derek’s cock strained against his jeans, wanting the same thing as Stiles. “Okay, turn around on the bed.” 

“Okay,” Stiles said, kissing Derek one more time on the mouth before Derek got off of him. Derek exhaled loudly as he unzipped his jeans. It didn’t surprise him as Stiles did the same, slinking out of his jeans where he lay on the bed, his own briefs with a wet spot soaked into them from his cock. 

“It was uncomfortable,” Stiles mumbled as he wiggled on the bed, moving his limbs around to get situated. He looked up at Derek with his hands on his stomach, waiting. Derek palmed himself as he stepped out of his jeans and briefs. He wasn’t fully hard yet, which could be a good thing for Stiles. 

“Open your mouth, cover your teeth with your lips,” Derek sat as he stepped forward, moving Stiles’ head, tilting it back. “Take hold of my thigh and if, for any reason, you need to stop, pinch me.” 

“Okay,” Stiles said. 

“Most of all, relax.” Stiles visibly let his body go slack as Derek stepped forward, brushing the head of his cock against Stiles’ lips. Derek groaned at the way Stiles’ mouth opened up for him as he slid the head of his cock inward shallowly. Stiles closed his eyes as he lay there, his body reacting to every shift in Derek’s movements. He played with a nipple as he slowly worked Stiles’ mouth. He pulled back, holding on to his cock, guiding it back in again after Stiles caught his breath, his mouth already reddened and wet with spit. 

“You’re doing so good,” Derek praised as he pushed further into Stiles mouth. Reflexively, Stiles spread his legs, his grip on Derek’s thighs tightening as Derek held on to Stiles’ head, pressing a thumb against his throat going even deeper before pulling out again. Stiles coughed, his eyes tearing up as he gasped for air. He looked up at Derek as his hands slid up Derek’s thighs, his mouth opening with his tongue peeking out as he asked for more. Derek obliged him, skimming his cock over Stiles’ lips before plunging in, hitting the back of Stiles’ throat and sinking deeper. Derek groaned as he felt his cock slide down Stiles’ throat. “Just like that,” Derek encouraged him as he thrust his hips experimentally. Stiles tapped his hand, and Derek immediately pulled back.

Derek wiped his hand over Stiles’ mouth, his dick spit-slick hanging heavy between his legs as Stiles breathed, his chest heaving as he wiped at his eyes. 

“Enough?” Derek asked him. Stiles nodded his head as he coughed. 

“Is that okay?” Stiles asked, his voice hoarse. It made Derek’s cock jerk, knowing he was the one who made Stiles’ voice so raw. Derek bent over, cupping Stiles’ face with both hands, then kissed him filthily, his mouth open as his tongue sought out Stiles’. Stiles’ mouth tasted of precome, wet and the kiss sloppy as Derek slid his hands down Stiles’ chest, pinching his nipples. Stiles moaned against Derek’s open mouth as his hands groped Derek’s thighs. The angle was odd, with Stiles on his back and Derek standing up, bent over in front of him, but as Stiles began moving against the bed, fucking up into the air, Derek ended the kiss. 

“Let’s see what you can take,” Derek said as his hand slid down Stiles’ stomach, his nails raking across the trail of hair disappearing beneath his precome soaked briefs. The sight of it had Derek leaking with want. 

“Okay,” Stiles said as he sat up. “Yeah, I want to show you.” Derek smiled at that, at Stiles wanting to be opened up for him. 

“Come here,” Derek said as he hooked his hand around Stiles’ neck, bringing him forward, their mouths crashing together as Derek got Stiles to stand up. Stiles pressed his body against Derek, wrapping his arms around Derek as they kissed. Derek slid his hands down Stiles’ back, his fingers slipping beneath his briefs, gripping his ass. Stiles rut against him, moaning as he lifted himself up, practically jumping up onto Derek, his legs hooked around his body. Derek’s cock pressed against Stiles’ as Derek slid a finger between Stiles’ asscheeks. 

“Fuck,” Stiles said against Derek’s mouth. “God, I really fucking--” 

He didn’t finish his sentence before they both crashed onto the bed. Derek was strong, but Stiles was tall, lanky, and not that light. 

“Let me go get everything,” Derek laughed as Stiles clung to him. 

“Like what?” Stiles asked as he mouthed at Derek’s neck, his thumb caressing Derek’s nipple piercing, sending a shiver down his back. 

“You’ll see. Get those off,” Derek said as he snapped the waistband of Stiles’ briefs as he got off the bed. He walked into the bathroom, grabbing a towel, then got his giant rubbermaid storage box out of his closet, going through it as quickly as possible. He must have taken longer than Stiles wanted, because Stiles walked into the closet, leaning over Derek. 

“Holy shit, it’s like a treasure chest of sex toys,” Stiles said as he put his hand on Derek’s shoulder. Derek snorted as he handed Stiles the towel. 

“Put that down on the bed,” he said as he also handed Stiles a tub of lube as opposed to the SILK. “And open this and put it on the bedside table, please.” 

“Wow, this is intense,” Stiles said as he read the label. “Boy Butter?” He laughed. Derek lifted an eyebrow at him. “I’m going, it’s just a funny name.” 

“You’ll appreciate it soon enough,” Derek said with a wry smile. He watched Stiles walk back into the bedroom before he began searching the bin more. When he found what he was looking for, he set the toys down on the counter. Beneath the sink he kept his toy cleaner, along with his condoms and rubber gloves. “Did you clean up, by chance?” Derek called out. Stiles walked back into the bathroom, leaning on the doorframe as Derek rinsed the toys after spraying them down. 

“Yeah,” Stiles said, his cheeks reddening. “In hopes of you know, us getting to do this.” Derek gave him an easy smile. His erection flagged, but that wasn’t a problem. Seeing Stiles stand there, naked, with his arms crossed made Derek grin. He looked like he belonged there, with him. “So what have you got there?” Stiles asked. “Plugs?” 

“Yeah, I want to see if you can take this one,” Derek said, showing Stiles one that is slightly bigger than the medium sized one he bought in his set. Stiles bit his lip, his eyes wide as he nodded his head. 

“Maybe,” Stiles said as he walked forward. “I trust you with me.” Derek kissed him as he picked up the toys. 

“Bring the condoms,” Derek said as he walked into the bedroom. Stiles tossed the box of condoms onto the bed before he climbed on, sitting with his legs crossed as he waited for Derek. Derek thought it endearing, how Stiles waited, watching him put down the toys. “Let’s see you on your back, show off some of that yoga.”

Stiles laughed, rolling his eyes as he did as Derek asked, lifting his legs as he spread them, showing Derek his ass. Derek groaned as he put on a pair of gloves. 

“Gloves?” Stiles asked, his neck craning so he could watch as Derek fixed them on his fingers so they felt okay. 

“Safer,” Derek said. “For the both of us.” 

“Okay,” Stiles said as he squirmed in place, trying to get comfortable. He sighed as he watched Derek roll on a condom to the three plugs he cleaned. “Condoms on those too?” 

“They’re mine, I feel better with the protection,” Derek explained. “It’s easier clean up, too.” 

“Should I do that too?” Stiles asked as Derek dipped two fingers into the lube, slicking his fingers up. 

“If you want,” Derek encouraged. “Do me a favor and grab one of my pillows and toss it onto the floor?” Stiles stretched an arm out, grabbing hold of one of Derek’s pillows, putting it on the floor at his feet. Derek knelt in front of Stiles as he re-situated himself. “You ready?” Derek asked. 

“For you to touch me? Yes,” Stiles groaned as he held onto the back of his thighs, holding his legs up. Derek bent over, licking up Stiles’ cock as his thumb circled around Stiles’ entrance. Derek buried his face against Stiles’ groin as he pressed inwards, only to pull his thumb back out again, replacing it with an index finger. Stiles panted, letting out a small whimper as Derek began to move his finger around, smearing lube around. 

“Oh god, having someone else touch me is never going to get old, holy shit.” Derek sat up so he could watch his finger disappear into Stiles’ ass then reappear again, over and over. When he was sure Stiles was ready for it, it pressed a second finger in, enjoying the litany of noises that escaped from Stiles’ mouth with each movement. Stiles wasn’t quiet, and as Derek crooked his fingers, Stiles shook, his legs dropping onto the bed as Stiles gripped the sheets beside him. He moved against Derek’s fingers, rolling his hips, fucking himself slowly on them. “Shit,” Stiles said with a breathy smile as he lifted his head, looking at Derek. “That’s just fingers and I’m about ready to come.”

“Do you need the cock ring?” Derek asked seriously. “Do you want it?” 

“No,” Stiles said as he shut his eyes, letting his head drop down back onto the bed. “If I come, I come. Keep going.” Derek licked up his cock once more, lapping at his head, sucking up a drop of precome that surfaced as Derek fucked him with his fingers. Stiles shuddered against him, his stomach tightening as he spread his legs further. He was coming undone before Derek, and it made his own erection reemerge. 

“Ready for the first plug?” Derek asked him. Stiles nodded his head, his eyes remaining closed as he lifted his legs once more. 

“Yeah,” Stiles said, sighing when Derek pulled his fingers out. “God, I feel so fucking empty right now.”

“That’ll change in a minute,” Derek said as he grabbed the toy, applying lube to it, smearing it around before pressing it up against Stiles’ opening. 

“Oh god,” Stiles said as it slid in. Once it was flush with Stiles’ ass, the base of it the only thing showing, Derek wrapped his hand around Stiles’ cock, jacking him off slowly. Stiles bit his lip as his back arched, his feet back on the mattress again as Derek twisted the plug within him. “Shit, shit, shit,” Stiles shouted as he came, his body seizing at the ferocity of his climax. Come covered his chest as Derek pumped the plug in and out of him shallowly, then pulled it out completely. Derek watched as Stiles’ ass closed up, red and slick with lube. 

“Do you need a break?” Derek asked as Stiles lay limp before him. Stiles shook his head as he licked his lips. 

“No, I want to be fucked,” Stiles said simply. Derek held back what he wanted to say, because he had no intention of doing that just yet, but he would open him up further if he wanted to be.

“Okay,” Derek said as he stood up, his lips finding Stiles’ before he licked up Stiles’ chest. 

“Oh god, I always thought that was something people just did in porn,” Stiles said as he moaned at Derek cleaning him up. “Fuck, that’s hot.” 

“Not just in porn,” Derek said as he reached for the medium sized plug. “I have an idea,” he said, catching Stiles’ eye. 

“What,” Stiles asked, his voice barely audible. 

“How long have you worn your plug?” Derek asked. 

“Like at a time?” Stiles asked. Derek nodded at him as he slicked up the toy, readying it for use. “Not that long,” Stiles said, his cheeks reddening. “What do you have in mind?” 

“I’d like to see how long you can wear it,” Derek asked, his voice hoarse as he thought about it. “Maybe if we watched a movie...”

“Okay,” Stiles said. “Let’s do it.” Derek kissed him again, he couldn’t help himself. Stiles was so open to try anything, it made Derek swell with something akin to pride, and it was all for Stiles. This time, the plug took some maneuvering before it slid into place, stretching Stiles as it sunk inwards. Stiles groaned as Derek took off the gloves, standing up to get a wet wipe to clean Stiles up with. 

When he returned and cleaned Stiles up, he dug out a pair of sweats for each of them, and two t-shirts, well worn and comfortable. Derek kissed Stiles into a standing position, letting Stiles moan into his open mouth as he cupped his face. 

“You okay?” Derek asked him. 

“So full,” Stiles whimpered as he snaked his hand around Derek’s torso. “God I’m so--” Stiles buried his face against Derek’s shoulder. “The others are bigger than this?” 

“Yeah,” Derek whispered as he rocked Stiles back and forth, pressing his cheek to Stiles’ head. “We’ll work up to them, come on.” Derek lead Stiles slowly towards the couch. “Let’s watch _Iron Man 3_. 

“You know me so well,” Stiles said with a grin as they sat down with no space between them. The movie barely began before Stiles’ mouth was on his neck, his hand slipping beneath the fabric of Derek’s sweatpants. 

“You don’t need to--”

“You didn’t get to come,” Stiles said as he nipped at Derek’s earlobe. Derek didn’t know how to explain that it wasn’t uncommon for him, that he was used to it, putting others’ pleasure before his own. As Stiles sat there, his legs practically in Derek’s lap, Derek ran his fingers across Stiles’ short hair, smiling lazily as he kissed him again. 

“We’ll take care of me later.” Stiles, his eyes glassy, pupils dilated, rest his head against Derek’s shoulder and sighed, his fist clenched in Derek’s shirt.

**Notes for the Chapter:**

> it was brought to my attention about the fact that "boy butter" isn't condom safe. I did research, and derek probably used one of these two products, which still has the name boy butter in them.... stiles was just reading what he saw pop out at him: [you'll never believe it's not boy butter](http://www.boybutterlubes.com/productinfo.html) or [boy butter clear h20](http://www.drugstore.com/boy-butter-clear-h2o-condom-safe-personal-lubricant/qxp391399)! I just wanted it to be made clear that Stiles only read PART of the label, as he was a little bit distracted!
> 
> I am well aware that normal boy butter is not condom safe. Before using any product please read all labels to make sure you are using them correctly!


	6. Chapter 6

**Notes for the Chapter:**

> happy (hiatus) Moonday :)

Stiles couldn’t concentrate on the movie at all. His body throbbed, a low level sort of pulse that kept him aware of every single movement he made. The plug was a constant reminder, the pressure immense as he tried to ignore it. The task seemed impossible as Stiles situated himself in a way that he could easily rut against Derek’s thigh. He needed the friction, craved it even as he thought about Derek’s fingers, his mouth, all with Derek sitting beside him. 

“Stiles,” Derek drawled, giving Stiles a look from over his glasses. Stiles wanted to move against him more, get himself off just by rubbing against his leg. Stiles groaned as Derek groped his ass, rubbing his hand against the base of the plug. 

“That isn’t fair,” Stiles said with a gasp. He shifted, stradling Derek’s lap as he ran his fingers through Derek’s hair, yanking on it. “This is driving me crazy.” 

“Do you want to take it out?” Derek asked. 

Stiles bit his lip as he shook his head, moving his hips against Derek’s lap, moaning as he sought some sort of friction. He was so horny he could barely stand it. Derek palmed his ass, pressing his fingers against the base, changing the angle of it. Stiles shouted as it brushed against his prostate. 

“No, no, no,” Stiles groaned as Derek mouthed at his exposed neck. “Fuck.” Stiles went from never being touched by someone else to needing Derek to have his hands on him at all times in a matter of days, and Stiles knew it was crazy, but he didn’t want to go back to the way it was before. He didn’t want to think about making himself come, or doing streams to feel confident in himself. He wanted Derek to make him feel good. 

Stiles moaned as Derek shoved Stiles’ borrowed sweatpants down his thighs, exposing his erection and his ass to Derek. Derek tapped a finger against the plug, making Stiles jolt forward as he looked down at Derek. The sun was gone, set behind the buildings surrounding Derek’s loft, and Stiles knew he had to think about the fact that his dad wanted him home at a decent hour so they could spend time together, but he couldn’t think straight as Derek managed to get his fingers between Stiles’ ass and the plug, pressing against Stiles’ cheeks. It was like Stiles’ brain short-circuited or something as he wrapped a hand around his own erection as he sought out Derek’s mouth, moaning once their lips crashed together. 

“Derek,” Stiles said against his lips. “I want to try the next one.” Derek grunted against him, shoving his own sweatpants out of the way, sliding his erection against Stiles’. “After this, this is good.” He wrapped his hand around both of them, jacking them both off together as he fucked his own hand. 

“Lube,” Derek said as he stretched towards the coffee table where the SILK sat. Stiles didn’t complain as Derek pumped it directly onto the head of his cock for him to spread around with his fingers. The slide of his hand over their cocks became easier, smoother within seconds. Stiles looked down between them, at Derek’s cock flush against his own. He groaned as Derek kneaded his fingers against Stiles’ ass as he mouthed along Stiles’ shoulder. 

Stiles watched the head of his cock disappear then reappear in his fist as Derek’s stayed visible, showing their size difference. Stiles shuddered as he thought about being fucked by him, spread wide and pushed against Derek’s bed. With Stiles’ free hand, he pushed up Derek’s shirt, getting it out of the way before he came all over Derek’s chest. Derek groaned, pressing a finger against Stiles’ entrance, slipping it between the plug and the edge of his hole. 

“Shit, shit, fuck, I can’t--” 

Stiles groaned as he pressed back at the intrusion, the stretch more than he was ready for. Derek kissed him, covering his moans with his mouth as his cock jerked in Stiles’ hand as he came, covering Stiles’ hand with come.

“You sure you want to move up?” Derek asked, his chest heaving as he rubbed Stiles’ back, Stiles’ head resting on Derek’s shoulder as he shook his head back and forth. 

“I don’t know,” Stiles said weakly; he was spent. 

“We don’t have to, we can take our time,” Derek said as his hand rubbed circles in Stiles’ back. He pulled at the base of the plug, taking it out of Stiles slowly. Stiles whimpered, oversensitized as he pressed his head against the back of the couch cushion, holding on to Derek. Derek covered Stiles’ entrance with his fingers, feeling how open he was, feeling him slowly close up. Stiles licked his lips as he contracted his muscles for Derek, making him groan as he felt them move. “God, Stiles, you just can’t do that and expect me to be okay,” Derek said as he mouthed at Stiles’ neck, marking him. 

Stiles sat there in Derek’s lap, letting Derek’s mouth trail over his neck. He felt empty, but he knew the feeling wouldn’t last. Eventually, Derek sat back on the couch, his hands slowly roaming over Stiles’ body. 

“Do you want to shower before you head home?” Derek asked some time later. Stiles hadn’t moved as he listened to the movie. Derek hadn’t complained about Stiles staying in his lap,but as Stiles sat up he saw that Derek had his eyes closed, his hands on Stiles’ thighs, unmoving. 

“Is that an invitation for you to join me?” Stiles asked. Derek’s mouth quirked upward as he opened one eye. 

“Depends on when you have to leave by,” Derek supplied. Stiles groaned as he buried his face against Derek’s shoulder, his hands slipping between the couch cushion and Derek’s back, holding him close. He didn’t want to leave. “I’ll join you, but you have to let me up to take a piss first.” 

Stiles climbed off of him, stumbling as he tried to stand. After kneeling for that long, his legs didn’t seem to want to work right. He waited until Derek opened the bathroom door before he walked in, the shower water already running, steaming up the bathroom. It was a stand-alone shower stall, big, more than enough room for the both of them. Stiles stepped in, moaning at the feeling of the water as it hit him. He hadn’t realized how cold he had been. As Derek’s arms wrapped around his body, Stiles leaned against him, his eyes closing as the water washed over them. 

“You going to wash me?” Stiles asked as Derek’s hand slid down between his cheeks. Derek raked his teeth across Stiles’ neck before nipping at his earlobe. 

“Do you want me to?” Derek asked. Stiles nodded his head as he felt his cock stir between his legs. Stiles watched as Derek grabbed the shower gel, pouring some into his hands before smearing it across Stiles’ stomach, cupping his balls and crotch as he lathered him up. His fingers slipped between Stiles’ ass cheeks, washing away the lube. Stiles tilted his head back against Derek’s shoulder, his mouth hanging open as Derek pressed a finger inward. 

“You make the best noises,” Derek said as he removed his finger. Stiles grunted as Derek pressed him against the tiled wall, his hands spreading Stiles’ cheeks with both hands. For a moment, Stiles wondered what Derek was about to do, but as he felt Derek’s cock slide between his cheeks, he moaned. “I’m patient, I’ll wait for you to be ready to take my cock,” Derek said, his breath hot against the back of Stiles’ neck as Derek thrust his hips against him. “But I can’t deny how much I want you.” 

“Fuck, Derek,” Stiles said as he managed to stick his ass out, giving himself enough room to wrap a hand around his own leaking cock. “I wish I was ready.” Derek teased at Stiles’ opening, pressing the head of his cock there. Stiles jerked upward onto his tiptoes, spreading his legs more. He wasn’t ready. Derek moved against him, his cock angled upward as it slid between Stiles’ cheeks. Stiles heard the cap of the shower gel being opened again as Derek took a step back. Stiles craned his neck, looking behind him as he watched Derek stroke his cock, using the shower gel to help the slide as he pressed his cock between Stiles’ legs. 

Stiles backed up against Derek’s chest, putting his legs together as Derek held him close, thrusting his dick between Stiles’ thighs, hitting the back of Stiles’ balls with each movement. Derek’s hand replaced Stiles’ as it jacked him off. Derek bit down on Stiles’ shoulder as Stiles looked down at his cock in Derek’s hand, water cascading down his body. 

The feel of Derek against him, every movement, made Stiles shake in anticipation of how much it would be intensified if he were actually being fucked. As much as he loved the feel of Derek’s cock between his legs, he wanted more. Stiles turned his head, seeking out Derek’s mouth. He got a mouthful of tongue and water as he closed his eyes, shielding them from the spray. Derek grunted, his thrusts becoming stilted as he came between Stiles’ legs. Stiles, too, came as Derek’s pace quickened. He pushed at Derek’s hand, not wanting to be touched anymore, it was too much. 

Derek took the hint, spinning Stiles around so they could keep kissing as their come washed off his body. When they got out of the shower and dried off, Stiles didn’t want to leave. As he got dressed, he checked himself out in the mirror. With the shower, he didn’t look nearly as debauched as he would have otherwise, but his cheeks were still flushed, and his lips were swollen. There, on his neck, was a hickey forming. Stiles covered it with his hand, looking to Derek who had his sweatpants on. 

“Oops,” Derek said as he put his glasses back on, smirking. “Next time I’ll aim lower.” 

Stiles snorted, but couldn’t help but think about a next time, and Derek marking him again. 

“Next time, I’ll do the marking,” Stiles said with feigned confidence. 

Derek lifted an eyebrow, but smiled. “I’d like that.” 

“You would?” Stiles asked as Derek stepped forward, kissing him. 

“You’d be surprised how much,” Derek said against his lips. “You should go, though.” 

“Yeah,” Stiles said, but didn’t budge as he continued to kiss Derek, running his fingers through Derek’s wet hair. “I should.” 

His dad was home by the time he pulled up. Stiles barely stepped foot inside the door before his dad appeared from the kitchen, his eyebrows raised in question, his gaze scanning over Stiles and stopping at his neck. 

“You got something to tell me?” He asked Stiles as he sat in his chair, his head tilted as he waited. Stiles cleared his throat, then scratched the back of his neck. 

“Well, uh, I’m sort of seeing someone,” Stiles said as he put his hands in his pockets. 

“I can see that,” the Sheriff said. “You going to tell me about them?” He asked. Stiles blew air out of his mouth, puffing out his cheeks as he thought about the best way to tell his dad that he was seeing someone nine years older than him. 

“Well, you see, uh--”

“We talked about this, Stiles,” he said. “About how I just want to know where you go, if you’re not at the McCalls’.” 

“I know,” Stiles said, looking to the floor. 

“So when you told me you were at Scott’s, but your Jeep wasn’t parked outside their house when I went on patrol... what do you think that tells me?” 

“That I lied,” Stiles said lowly, biting his lip. He lied to his dad because Derek is twenty-seven, and he’s eighteen. The sheriff gave him a look. “Look, Dad, his name is Derek, and I really like him, but we haven’t talked about parameters or labels and I don’t want to make a big deal out of nothing.” 

“Derek who?” His dad asked. Stiles crossed his arms as he tapped his foot. If he gave his dad Derek’s full name, he’d look him up. 

“Dad, no,” Stiles said. “Privacy.” 

“I just want you to be safe.”

“We are being safe,” Stiles said, dropping his arms, his cheeks flushing a deep red when he realized what he just said. His dad’s eyes widened, but said nothing as he gripped the arm rest. “I swear,” Stiles added. 

“I will leave you alone if you promise me you will be home by ten every night.”

“Ten? What? I haven’t had that curfew since ninth grade--” Stiles shut his mouth when his dad held up his hand. “Okay.”

“I want an open line of communication between us, okay?” 

“Yeah,” Stiles said, nodding his head. “I’m gonna go upstairs,” he said, pointing towards the stairs. When he got to his room, he shut the door, sighing as he leaned against it. Eventually, he made his way back downstairs, ready to spend the evening with his dad. When he asked if Stiles wanted to watch _Iron Man 3_ , Stiles said yes because technically he hadn’t paid attention to the screen earlier.

He couldn’t stop thinking about Derek the entire movie. 

Stiles spent the weekend writing a paper, playing video games with Scott, and pointedly not making a trip out to the store. He didn’t want to seem clingy, or that he didn’t have other stuff going on. Derek seemed fine with the space, texting a few times, but nothing in regard to hooking up again. On Sunday night around seven, Stiles caved and made his way into town to the art gallery. He got coffee first, before he walked into the gallery where Derek was hunched over his sketch pad. 

When Derek looked up at him, he smiled. It made Stiles’ stomach do somersaults. 

“Hey,” Stiles said as he leaned against the counter. 

“Hey yourself.” Derek sat as he put the pencil he was using down. “I wasn’t expecting you.” Stiles looked Derek over as his stomach plummeted. He wondered if he wasn’t welcome, if Derek wanted more space. He wore a v-neck shirt, showing off his tattoos, along with his well worn jeans. He looked comfortable, at ease. Stiles wished he felt that way, but his body was too lanky, too uncoordinated. “It’s a nice surprise,” Derek added, leaning forward as he caught Stiles’ gaze. 

“I needed caffeine to finish a paper,” Stiles said, finally looking up. He wanted to kiss Derek, but wasn’t sure what he was doing. He didn’t know what they were, and all they had done was mess around, always at Derek’s.

“What’s it about?” Derek asked. 

“It’s about the Napoleonic Wars,” Stiles said, sighing. “It’s due tomorrow and I’ve still got a few hours left to go.” 

“So you just stopped by for a minute,” Derek said, raising his eyebrow, leaning forward. Stiles’ heart skipped a beat as he mirrored Derek’s movement, kissing him. 

“Something like that,” Stiles said as he kissed him again. “Hey, I was thinking,” he said as he sat up straighter, looking at his coffee instead of directly at Derek. “What if we went out sometime?”

There, he said it. It was out in the open, that he wanted to. Derek sat up, his fingers drumming against the countertop as he looked at Stiles. 

“Yeah,” Derek said, his brow furrowing. “We could have gone out this weekend. I didn’t think you wanted to.” Stiles sputtered, his jaw dropping. 

“What? Yeah, I do, that’s-- that’s what I want.” 

“We can do that,” Derek said with an easy smile. “I’m off on Wednesday, we can go then if you’re free. Otherwise I work nights here.” 

“Wednesday it is, then,” Stiles said with a grin. “It’s a date.” Derek chuckled, nodding his head. 

“A date.” 

Three days of school seemed like some sort of punishment. Stiles was in the homestretch of school, he could see the light at the end of the tunnel, and yet all he could think about as he watched the clock on Wednesday afternoon was that this was the longest week of his life. He didn’t even stop at his locker before he made his way to the parking lot, rushing to get to his Jeep before the way out was blocked by other cars. 

At home, he got directly into the shower after dropping his things off in his room. When he was done, Stiles realized that he had a few hours before they were supposed to meet up. Wearing a pair of briefs, Stiles sat in front of his computer to check his emails. For the porn website he streamed on, he made up some name, and an email to go along with it instead of his real name. He hadn’t logged into the email since his last stream, which had been the one that Derek watched. 

Stiles had over one hundred emails, most of which were messages from the site’s messaging system asking him when his next stream would be. Some were nicer than others, considering one was in all caps asking why he hadn’t been around. Stiles deleted most of them as he browsed through them, his eyebrows lifting at the wording at some of the messages.   
The gist of it was simple: they wanted him to be fucked. Some offered to do it, sending him pictures and locations. Stiles saw a lot of dick he hadn’t intended to see. 

“Jesus,” Stiles said as he deleted one saying they wanted to tie him down and gag him as they fucked him. “No thank you,” he said to himself. “Do not want.”

He didn’t want anyone else touching him, he realized, when all the emails were gone. Stiles sighed, running his hand over his face. He was about to get up when there was a knock at his door. His dad walked in, not at all surprised to see Stiles sitting there almost naked. 

“I’m heading in, I just got a call. Are you staying in tonight?” He asked. Stiles bit his lip, because he hadn’t told his dad about his date. 

“No, I’m going out. I have a... date.” 

“With that Derek?” His dad asked. Stiles nodded his head, clearing his throat as he looked at his lap. “I hope that’s not what you’re wearing,” he teased. Stiles laughed, covering his mouth as he caught his dad’s eye. 

“I just got out of the shower.” 

“Showering is good; very hygienic.”

“That’s what I was going for,” Stiles said. “We’re going to dinner.”

“Where at?” His dad asked. 

“The Mexican place down near the station,” Stiles said. “If I see a cop car drive by--”

“I’ll keep my distance, kiddo. You just remember--”

“Back by ten,” Stiles said with a smile. “I got it.” 

“Set an alarm.”

“I’ll be Cinderella, only without the evil stepmom.”

“Sure,” his dad said, giving him a look before leaving Stiles in his room alone again. Stiles turned back to his screen, seeing that five new emails popped up. Without even looking, he deleted them, groaning before he shut his laptop so he could get ready. 

He stood outside Mamasita’s, the one Mexican place in Beacon Hills that had a salsa bar. Obviously it was superior, so that was what he chose. He checked his phone multiple times, even though Derek was only five minutes late. When he saw the Camaro pull into the parking lot, he stopped worrying that Derek wouldn’t show up. It was silly to be so paranoid, Stiles knew that, but that didn’t stop the thought of being stood up from entering his mind and burrowing somewhere between memories of being denied chances and attending school dances alone. 

As Derek approached him, Stiles couldn’t help but admire the view: dark, almost black jeans, paired with a maroon, long sleeved shirt with holes in them for Derek’s thumbs to slip through made Derek look mouth watering. What surprised Stiles was the fact that it looked like Derek’s stubble was shorter, like he shaved a few days ago. When Derek got to him, he kissed Stiles with a smile on his face. 

“You look nice,” Derek said, which made Stiles scoff. He had on a plaid shirt and an X-Men shirt on. 

“Don’t lie,” Stiles said against Derek’s lips. 

“I wasn’t,” Derek said as he put his hand on Stiles’ lower back. “Batman is better than X-Men.”

“Are you DC or Marvel?” Stiles asked as Derek opened the door for them. 

“DC, actually,” Derek said as the hostess smiled at them both. “Table for two, please.” 

“Right this way,” she said, grabbing two menus before showing them to her table. 

“I knew you were a DC guy.”

“Couldn’t be because of my tattoo,” Derek said, which made Stiles’ jaw drop. 

“Which one? I didn’t see a DC tattoo--”

“I’ll show you some time,” Derek said. “It’s right here,” he told Stiles as he lifted his arm, pointing to a spot under his arm.

“I’ll check it out next time,” Stiles said as a waitress brought them chips. Stiles ordered a Coke, then went to the salsa bar, grabbing three different kinds of salsa before heading back to the table. 

Derek ordered a burrito the size of an infant, while Stiles got a quesadilla. They chatted about their week, crazy customers at the store, Stiles’ trigonometry test, and about Derek’s hours that week. Stiles couldn’t remember ever feeling so at ease with someone who wasn’t his friend, or someone he didn’t know for very long. Usually, he rambled when he was nervous but he didn’t feel any of that as they ate. He was halfway through his quesadilla when he saw it out of the corner of his eye: sheriff brown. He’d know the uniform anywhere. 

Stiles almost flipped out about his dad showing up, when he realized it was Kyle Parrish. Stiles’ eyes narrowed as his eyes locked with Kyle’s. Derek turned to look at who Stiles was having a staredown with, his face breaking out in a grin as Kyle approached. Stiles watched as they did some sort of handshake/bro hug. 

“What up, man?” Kyle asked Derek as he sat back down. 

“Nothing much, what are you doing here?” Derek asked. “Dinner break?” 

“Something like that,” Kyle said, giving Stiles a look. Stiles bit the inside of his cheek in attempt to keep his mouth shut. “Heard the Stilinski kid was on a date, decided to stop by and see what’s up.”

“You mean spy,” Stiles pointed out. “For my dad.” Kyle shrugged his shoulder, looking at Derek. 

“You guys going steady?” Kyle asked with amusement. Derek rolled his eyes at Kyle as Stiles bristled. Derek gave him a look that clearly said ‘calm down.’ 

“Poker night Friday?” Derek asked, changing the subject. Kyle seemed to relax, nodding his head. 

“Your place this time? 9:30?” 

“Yep,” Derek said as he ate a chip, dipping it in one of Stiles’ salsas. 

“Stiles, you coming?” Kyle asked. “It’s a twenty-dollar buy-in.” Stiles exchanged a glance with Derek, who gave him an encouraging nod.

“Yeah,” Stiles said as he nodded his head. He’d have to ask his dad, but since it was a weekend, he didn’t see why he couldn’t. “I am.” 

“Great,” Kyle said, winking. “I’ll leave you two to it.” 

As Kyle started towards the door, he decided to go after Kyle, catching up with him before he opened it. 

“Are you going to tell him?” Stiles asked. “My dad.”

“That you’re dating Derek Hale?” Kyle asked. “No way. That’s on you. He was worried about you is all. Derek? He’s my best friend. He’s good news, not bad. But telling your dad you’re boning someone not in high school is probably a good idea. He thinks you’re with some jock or something.”

“Oh,” Stiles said, taken aback. “Thanks.”

“No problem,” Kyle said, patting Stiles’ shoulder. “Make him buy your dinner. Don’t put out otherwise.”

Stiles laughed as he returned to the table. 

“Everything okay?” Derek asked. 

“Yeah,” Stiles said taking a sip of his Coke. “It’s great.” 

Derek did end up paying, which blew Stiles’ mind. He even walked him to his Jeep, kissing him on the cheek before Stiles dipped his head, finding Derek’s lips with his own, pushing Derek against the door to the Jeep. 

“Good first date?” Derek asked as he cupped Stiles’ face with his hands. Stiles nodded his head, kissing Derek once more. 

“Can’t go wrong with Mexican,” Stiles said, though his lips were on fire from the Sriracha he put on his quesadilla. Derek sucked on his lower lip before taking a step back. 

“I’ll see you Friday?”

“Yeah,” Stiles said, reaching out for Derek’s shirt, pulling him back in. “Poker night.”

“I’ll pay your buy-in,” Derek said, nosing at Stiles’ neck before placing a kiss over his faded hickey. 

“I can pay my own buy-in,” Stiles said, shoving Derek back playfully. Derek grinned at him, running his thumb over Stiles’ lips. 

“See if you can stay the night.”

“Okay,” Stiles said, his voice catching. “I’ll see.”


	7. Chapter 7

**Notes for the Chapter:**

> another moonday update!  
> how many chapters did it take for me to use the 'first time' tag though I mean really

The fridge was stocked, full of beer and a bottle of wine, for Erica, so the only thing left to do while Derek waited for his friends to arrive was to relax. He had music playing from his Smart TV, his sketch pad on the ground with charcoals surrounding it. Fresh from a shower, he thought about doing something less messy, but that never stopped him before. 

Derek wouldn’t say that he was nervous, not really. He felt a knot in his stomach, though, about Stiles meeting his friends. Sure, Stiles knew Erica and Kyle, but that didn’t mean he _knew_ them, not like Derek did. Likewise, he didn’t know how his friends would react to the fact that Stiles was a teenager. 

It was a recipe for disaster, truthfully, but Derek decided to ignore it. 

By the time his door slid open, Derek had charcoal on his hands and shirt, smudged across his fingertips and smeared on his forearms. His older sister, Laura, walked in with a bag of snacks with Cora, his younger sister, trailing behind with a pack of hard cider. 

Laura had her hair done up in intricate braids, wearing a tank top that showed off her own tattooed sleeves. Derek stood up, wiping his hands on his already dirty shirt before he helped set everything out. 

“How many did you say?” Laura asked as she opened a bag of tortilla chips. 

“Um, at least six.”

“Big game of poker,” Cora said as she set out ingredients to make her ‘famous chili dip’ which was basically cream cheese, canned chili with beans, and cheese heated up in the microwave. 

“So that’s Cor and I, Erica, Kyle....” 

“Boyd, Erica’s boyfriend, and my-- Stiles.”

“Your Stiles?” Laura asked with a grin. 

“Stiles?” Cora asked. “Like Sheriff’s son Stiles Stilinski?”

“You know him?” Derek asked, not at all surprised. Cora wasn’t much older than Stiles, being nineteen. She opened a hard cider, her eyes narrowing. 

“Are you dating someone younger than me, Der?” Cora asked as she took a swig of her cider. 

“Are you drinking cider in my house?” Derek asked. “That’s appalling.”

“You’re a cradle robber,” Cora pointed out, but there was no heat behind her words. “He’s a little twinky, don’t you think?” Derek snorted as he washed his hands, using his shoulder to wipe at his forehead where there was an itch. 

“Everyone has a type,” Laura said with a sigh, winking at Derek. “We’ll play nice.” 

“Good,” Derek said as he dried his hands with his shirt. “I’m going to go change.” 

“Oh, wear that henley,” Laura called out as Derek ascended the spiral staircase. 

“Which one?” Derek called out from the top. 

“You know the one,” Laura said with a smirk as she grabbed herself a beer from the fridge, popping it open as she leaned against the counter. 

Derek could hear them talking to each other as he changed, tossing his shirt to the floor haphazardly before he searched for the grey, faded henley that Laura knew he had. It was old, soft, and had a certain way of hugging his body that had the general population on their knees before him if he wore it out. 

He slipped it on, looking himself over in the mirror once before heading back downstairs. When he got there, it didn’t surprise him to see Erica and Boyd there, with drinks already in hand courtesy of Laura. Erica had a glass of wine, while Boyd had one of Derek’s favorites. Derek, empty-handed, got one for himself. 

“What were you working on?” Erica asked as she walked over to Derek’s sketch pad, looking it over. 

“I was just messing,” Derek said with a shrug as he picked it up, closing it before slipping the giant pad behind the couch. “Waiting for you guys to get here.” 

“So, is he coming?” Erica asked with a wry smile. 

“He said he was,” Derek said, feigning nonchalance. He wasn’t nervous, not a bit. Erica lifted an eyebrow as she sipped her wine. 

“Look who I found loitering!” Kyle shouted as the door slid open. Derek turned his head to find Stiles, wearing a pair of khakis and a plain white t-shirt instead one of his graphic tees. Kyle had his hand on Stiles’ shoulder as he shook him. “I figured I’d bring him on up, since he looked lost.” Derek knew Stiles wasn’t lost, he couldn’t have been with the amount of times he had been there. 

“Don’t be a dick,” Derek said as he made his way over. Stiles’ eyes were on him and him alone. Derek saw Stiles look him over, his eyes catching on his chest, where it was most likely apparent that Derek had a barbell piercing. “Hey,” he whispered, his mouth close to Stiles’ ear as he slipped his hand around Stiles’ waist. 

“Hey,” Stiles said, his voice shaking. 

“Guys, this is Stiles,” Derek said, looking at his friends, his family. “He’s going to be the one taking all your money tonight,” he said with a smirk. Stiles looked at him, jaw slack. Derek had no idea if Stiles even played, but the comment broke the tension in the room. Erica stepped forward, her usual grin in place. 

“I was hoping you’d make it,” she said as she booped him on the nose playfully. “What do you want to drink?”

Stiles looked to Kyle who was already at the fridge. 

“You driving tonight?” Kyle asked, faux seriously. 

“No, sir,” Stiles said out of habit. Derek saw Laura cover her mouth out of the corner of his eye, holding back a laugh. 

“Then let’s get you smashed.”

Kyle handed Stiles a beer, even opened it for him, before walking over to Boyd. 

“Are you sure?” Stiles asked as he looked at the beer. Derek, his hand still around Stiles’ waist, sliding up and down his side as he nodded his head. 

“You staying here?” Derek asked, barely audible. Stiles nodded his head as his teeth caught his bottom lip. 

“My bag is in my Jeep.” Derek smiled because Stiles _packed_. 

“Then drink up. I won’t tell, neither will Kyle. Cora’s drinking, too.”

“Cora?” Stiles asked, his eyes catching Cora’s. “Hale. Of course.” As if on cue, Cora and Laura walked over, their drinks in hand, both of their heads tilted as they looked Stiles over. 

“Stilinski,” Cora said with her arms crossed, her bottle cradled in her hand. “Have you met Laura?” 

“No, hi,” Stiles said as he shook Laura’s hand. “Stiles.”

“Hi, Stiles,” Laura said warmly, her eyes catching his before they glanced to Derek. “He’s cute.” 

“Thanks,” Stiles murmured, subconsciously leaning against Derek. 

“So you guys know each other how?” Cora asked expectantly. Derek and Stiles exchanged glances, searching each other’s expressions. 

“The gallery,” Stiles said, his eyes lingering on Derek’s lips. “Next to the coffee shop.”

“Don’t forget the store,” Erica said plainly. “Well, that’s how _I_ know Stiles.” 

“Oh, so you _are_ eighteen, then,” Cora said, smirking. Derek felt like throttling her. Stiles laughed as he took a sip of his beer. 

“Yeah, I am.” 

“He came into the store on his birthday,” Derek supplied. Stiles sputtered, coughing a little bit. 

“Aww, that’s so cute,” Laura said, making a face that was normally saved for looking at kittens and puppies. “You can stay.”

“Thanks,” Stiles said, putting a hand on Derek’s waist after sighing. He slipped his thumb through Derek’s belt loop, holding on. Derek pressed his lips against Stiles’ head, giving him an encouraging peck. 

“Who wants to play poker?” Derek asked, his voice filling the loft. 

“I’m going to rip y’all a new one,” Kyle said as he took a seat. Derek didn’t have a kitchen table, but he did have a poker table that he usually kept folded up in the closet. He had folding chairs, too, enough for everyone to sit. Boyd put a few beers on ice in a cooler to keep between him and Derek, so they didn’t have to keep getting up in the middle of the game. 

“Alright, guys, give us your money,” Erica said as she put the lock box on the table; it was small enough to hold the cash. Derek threw his on the table, trying not to grin as Stiles placed his carefully over Derek’s, a wad of ones and two fives. 

Derek shuffled the cards as Erica set about giving everyone chips. 

“The game is Texas Hold'em,” Derek said as he looked around the table. “Everyone know the rules?” Everyone nodded as they looked at Stiles, just to see if he did. 

“Yep,” Stiles said as he popped the ‘p’. The corner of Derek’s mouth lifted as he placed the cards in front of Stiles. 

“Cut?” Derek asked. Stiles took the top half of the cards, then split the pile in two. Derek put what was the bottom of the stack on the top, then shuffled them again before dealing. 

Derek had a good buzz going two hours later. He was doing rather well, considering Kyle already had to buy back in. Stiles was still in the game, though barely, while Cora had a pile of chips in front of her. Erica played safe as she nursed her wine, the bottle almost gone. 

If they didn’t have a no hands under the table rule, Derek would take advantage of the fact that Stiles’ thigh was pressed against his, his leg bouncing as he dealt the cards. 

“Call,” Boyd said, then looked to Derek. Derek sighed as he looked at his cards, then at the ones laid out on the table before them. 

“Fold,” Derek said as he placed his cards face down on the table. Stiles bit his lip, then grabbed one of his few remaining chips. 

“Raise,” he said. Unable to hold back, Derek leaned over to see Stiles’ hand. It wasn’t good form, but Stiles showed him without thought. All diamonds, with two diamonds on the table. Shit. The pot was big, one of the biggest hands they had, and Derek felt Stiles’ tension as Erica flipped the last card over. 

It was a queen of diamonds. 

Derek kept his grin to himself as Stiles bet against Boyd. After Stiles turned his cards over, revealing his win, Derek smiled, his hand clapping Stiles on the back when Boyd threw his cards down, cursing under his breath. 

“Damn you, Stilinski,” Cora hissed as Stiles reached out across the table, gathering his chips with a grin on his face. He caught Derek’s eye, then leaned in, kissing Derek. 

“Well, Derek was right, we have to watch him like a hawk,” Erica said as Kyle gathered the cards to deal. Stiles laughed against Derek’s lips, then backed away as he carefully began to stack his chips. “Someone give him more alcohol.” 

Derek opened another one for Stiles, replacing it with his empty. 

“I’m out this round,” Derek said as he stood up. He got up, cleaning up the empties that littered the table and floor surrounding them, then made his way upstairs to his bathroom. He peed, then washed his hands, looking himself over in the mirror. 

Seeing Stiles with his friends, surrounded by them, and getting along with them made him ache. It had been a long time since Derek introduced anyone to his sisters, and he knew Stiles didn’t realize the impact of that. He didn’t know what it meant. Hell, Derek wasn’t even sure what it meant, but he did know that he cared about Stiles, more than he should. 

Stiles may only be eighteen, but age was just a number. He felt for him. Usually Derek ran at the first sign of attachment, of more than a one night stand or periodic booty calls. He could get sex, easily, with a press of a button, but what he wanted was Stiles. _Who_ he wanted was downstairs, laughing his ass off at some comment Derek couldn’t hear. Stiles, who did amateur porn and had never-ending questions about sex toys and was so eager to learn more. 

Derek ran his fingers through his hair as he turned off the bathroom light, emerging to find Laura there, waiting with her arms crossed. 

“You fall in?” She asked, indicating that Derek took a long time. Derek flipped her off casually, rolling his eyes at her. 

“My house,” Derek said simply. 

“He’s good,” Laura stated. 

“I told you he would take our money,” Derek pointed out, though he knew that wasn’t what she meant. Laura rolled her eyes at him. 

“He’s good for _you_ , asshole.” 

“You’re sweet,” Derek said, his voice dripping with sarcasm. 

“Dick.”

“Basically,” Derek said as he made his way down the spiral staircase. 

They played for another hour. He ended up out about fifteen dollars, which wasn’t a bad night. Kyle struck out the forty, which surprised no one. Stiles took home thirty, gaining him ten dollars more than he came with. Cora took home the most. Derek maintained that it was the cider. 

As he said goodbye to everyone, Stiles disappeared upstairs to seemingly use the bathroom. Derek cleaned up, washing off the countertops as he waited for Stiles to return. He must have lost track of time, because when he heard Stiles clearing his throat, he looked up to find him leaning against the ironwork railing, his hands dangling down. 

“Are you stalling or something?” Stiles asked, his voice carrying down into the kitchen. 

“I thought you were coming back down,” Derek said truthfully. It was only then that he realized that Stiles was without pants, his black boxer briefs peaking out from beneath his white shirt. “I’m coming up now.” 

Derek ascended the stairs two at a time, not at all surprised to find Stiles at the top waiting for him with his hands on his hips, his fingers touching bare skin as his shirt hid his crotch from Derek’s viewing pleasure. 

“I didn’t know you’d be so enthralled with cleaning--” Stiles began to say, but Derek interrupted by kissing him, his hands cupping Stiles’ face. Stiles breathed in as his hands gripped Derek’s shirt. “My bag is down in my Jeep,” Stiles said as Derek’s mouth trailed down Stiles’ neck. 

He slid his hands down Stiles’ body, grabbing hold of Stiles’ ass. Stiles groaned as his hands shoved Derek’s shirt out of the way so he could touch him. 

“God, you make me instantly hard, this is a problem,” Stiles said as Derek pressed a finger between his cheeks, making Stiles’ breath hitch in his throat. 

“I don’t see the problem,” Derek said as he mouthed at Stiles’ neck. 

“Hey, hey, about the marking--” 

Derek rid Stiles of his shirt so he could suck on his shoulder, his hands slipping beneath the fabric of Stiles’ briefs. 

“This clothing to bare skin ratio is a little off,” Stiles murmured as Derek walked him over towards the bed. “By like 75%.” 

“So undress me,” Derek suggested as Stiles tugged at his henley, tossing it to the floor. Stiles’ lip caught on his teeth as he fumbled with Derek’s jeans. As he slid them down Derek’s thighs, he sat on the edge of the bed, leaning forward to mouth at Derek’s stomach, his hands roaming Derek’s chest, thumbing over his barbelled nipple. 

Stiles looked up at him, as he pinched the nipple, his other hand on Derek’s hip as he sat with his legs spread. 

“What if... what if I wanted to eat you out?” Stiles asked, his pupils dilated. Derek groaned as he ran his fingers over Stiles’ buzzed hair, then down his cheek. Stiles chased his fingers, taking Derek’s thumb into his mouth teasingly. 

“You could do that,” Derek said, his voice not sounding like his own. Stiles grinned as he lay back on the bed. “Take your briefs off,” Derek said as he stepped out of his own. Stiles complied, but remained lying down. Derek’s brow drew downward as Stiles looked at him expectantly, his erection laying against his stomach, hardening visibly with each passing moment. “Do you want me to sit on you?’ Derek asked, his breath leaving his lungs, aching at the thought of it. Stiles nodded his head as he licked his lips. 

“Yeah,” he said, his voice quiet. Derek crawled onto the bed, kissing Stiles one last time. It was mostly tongue, which got Derek hard. The feel of Stiles’ tongue against his, the thought of it on his ass had Derek moaning, deepening the kiss. Beneath him, Stiles wrapped a hand around Derek’s cock, jacking him slowly until Derek broke the kiss, turning around to face away from Stiles. 

Stiles’ hands on his ass felt amazing, his long fingers digging into the flesh as he spread Derek’s cheeks wide. Stiles first drag of his tongue over Derek’s hole was tentative, slow. Derek hung his head low as Stiles licked up his cleft again and again, with each pass becoming more and more confident in his movements. When his tongue delved inwards, Derek moaned, pressing back against Stiles’ eager mouth. He felt Stiles’ nose brush against him as he moved, his tongue slipping in and out as his fingers spread him wide. 

“Fuck, yes, just like that,” Derek moaned as he leaned forward on his hands, rolling his hips back against Stiles’ mouth, his jaw hung open as Stiles licked and probed. It had been a while since Derek was rimmed, and Stiles’ mouth on him had him leaking precome onto Stiles’ chest. Derek smeared it down Stiles’ stomach, then wrapped his hand around Stiles’ erection. He leaned over, licking down Stiles’ length as he cupped his balls. Stiles’ legs spread, his knee falling to the side as he moaned against Derek’s ass. Derek moaned as he took Stiles’ head into his mouth, sucking at it, his tongue swirling over it before taking Stiles into his mouth fully. Once his lips touched Stiles’ pubic hair, Derek pulled back, a line of spit connecting his lips to Stiles’ dick. He licked again, savoring the taste of him as Stiles slipped a finger in with his tongue, making Derek groan at the intrusion. 

“Fuck,” he said as his cock twitched with interest. “Yes.” 

Stiles nipped at his ass, his teeth sharp as he bit down, then sucked as his finger fucked him. Spit was enough for one, but if Stiles wanted to do more, they’d have to get the lube. Stiles seemed content with just the one finger as he went back and forth between using his tongue and his index finger, teasing Derek as Derek blew him. 

“I want you to fuck me,” Derek grunted. He wanted to be fucked by him, down into the mattress. As he took Stiles into his mouth once more, Stiles shook beneath him, fingers against Derek’s ass as he gasped aloud. 

“Fuck,” Stiles said as he came down Derek’s throat. Derek swallowed all of him, licking the remains as he rolled his hips against Stiles’ fingers, seeking more from him. “Don’t say shit like that.” 

Derek twisted around, facing him finally, running a thumb over Stiles’ reddened, swollen lips. He wanted to kiss him but wouldn’t. 

“It’s the truth,” Derek said as Stiles closed his eyes, his fingers raking up Derek’s thighs. 

“Give me a few,” Stiles murmured, his eyes opening, lids heavy. He pulled Derek down onto the bed, where he lay out next to Stiles, his cock rubbing against Stiles’ thigh as he draped a leg over him. Derek mouthed at Stiles’ neck, behind his ear as his hand roamed Stiles’ upper body. 

“You’re shaved,” Stiles said, blinking as he moaned. Derek hummed as he removed his glasses. They were in the way as he marked Stiles’ shoulder as he moved against him, rutting against his body. 

“Yes,” Derek said as his fingers ran through Stiles’ happy trail, down to his cock, then back up again. 

“Why?” Stiles asked. “I mean, by your cock you’re trimmed, but your ass? Not your ass, but your hole--”

“It helps with everything,” Derek said as he felt Stiles’ stirring beneath the palm of his hand. “No hair means it won’t catch, makes everything slide in easier,” Derek told him. Stiles moaned as Derek fondled his balls, his legs spreading as Derek pressed a finger behind them. “It feels good.” 

“God,” Stiles said as his chest heaved. “That shouldn’t sound so fucking hot to me, but it does,” he panted. Derek could feel Stiles getting harder in his hand as he began stroking him. “Am I really going to fuck you?” Stiles asked. 

“If you want,” Derek said, thinking about riding him. He could take Stiles without much prep, it would be Stiles’ first time. He could make it good for him. 

“I do,” Stiles said, his face nuzzling against Derek’s shoulder and neck. He knew Derek didn’t want to kiss, not after rimming him, but that didn’t mean they couldn’t be intimate. 

“Let me get supplies,” Derek said, kissing Stiles’ cheek before getting up, his own erection hanging down between his legs. “Get yourself ready.”

He heard Stiles spit into his own hand to use as temporary lube as he grabbed a condom and real lube from the bathroom. He straddled Stiles, facing him this time, practically sitting in his lap as he messed with the condom. Stiles looked over the lube, reading the back of it which amused Derek to no end. Stiles slicked two fingers as Derek scooted up his chest, his cock right in front of Stiles’ face. 

As Stiles slipped one finger inward, Derek took hold of his dick, brushing his head over Stiles’ mouth. Stiles opened his mouth for him, his tongue lapping at his exposed head as he pressed another finger inward, stretching him. Derek groaned as Stiles fucked him with his fingers as he worked his mouth shallowly. Derek moved his hips against both Stiles’ fingers and his mouth, his stomach clenching at both feelings. 

When Stiles pressed in a third, Derek grabbed onto Stiles’ head, shoving his dick down deeper as Stiles crooked his fingers within him. 

“Shit,” Derek said, his breath shaking as he pulled back from Stiles’ mouth. “I think I’m ready for you.” 

Stiles looked up at him, his eyes glassy and pupils blown. 

“Want to ride me?” Stiles asked. “I don’t know if I can-- I don’t want to suck.”

“You won’t,” Derek encouraged him as he picked up the discarded condom packet. Stiles’ hands were on Derek’s thighs, fingers slick with lube. Derek rolled the condom on Stiles, jacking him off as he applied more lube before lining himself up. Stiles’ entire body stiffened as Derek sunk down onto his cock, moving slowly as his fingers remained holding Stiles’ cock in place so he could ride him. Stiles’ grip on Derek’s thighs tightened as he threw his head back, his mouth open wide. 

“Fuck, that’s nothing like the fucking--” Stiles groaned as he moved his hips, or attempted to, with no form of finesse. Derek ground his hips downwards, a hand on Stiles’ chest to hold himself up as he fucked himself on Stiles’ cock. “Fuck,” Stiles groaned again as a hand wrapped around Derek’s cock, jacking him without any kind of pace. He was uncoordinated beneath Derek, eager, and completely heartwarming as Derek moved. Stiles moaned, as did Derek as he found a groove he liked. Stiles let Derek set the pace as he rode him, feeling his own climax nearing. 

Stiles shouted as his hand stopped moving. He came, and as Derek rode him to completion, he panted beneath him, covered in sweat. As Derek pulled Stiles’ spent cock from within him, he wrapped his own hand around his cock, stroking himself towards his own climax as Stiles lay there before him. 

Derek came onto Stiles’ chest and chin, making a mess of him as he leaned over to lick it up. Stiles squirmed under him, his hands lazily trailing over Derek’s arms as he watched Derek lap up the mess. 

“I feel drunk,” Stiles said. “Come drunk, or something.” Derek snorted as he pulled Stiles up from the bed, taking him towards the bathroom. 

“Here,” Derek said, taking out a spare toothbrush and pointing towards the mouthwash. Stiles brushed his teeth without comment as Derek got out a cloth, wetting it to wipe them down. As Stiles gargled the mouthwash, Derek stripped the bed, changing the sheets. 

Stiles fell into the bed without a word, curling around one of the pillows as Derek brushed his own teeth. By the time he got into the bed, pulling a sheet over them, Stiles was passed out. Derek kissed Stiles’ bare shoulder as he lay down, wrapping an arm around him as he shut his own eyes.


	8. Chapter 8

Finding a balance between high school, homework, hanging out with Scott a few nights a week, seeing his dad, and spending time with Derek seemed like a feat that Stiles was unable to accomplish. His dad worked days, mostly, and wanted Stiles to be home for dinner with him. His nightly curfew of ten only worked for one week before his dad caved, letting Stiles have free reign once more as long as his grades didn’t slip. 

The first time Stiles brought homework to Derek’s, Derek gave him a dubious look. 

“Look, it’s either I write this paper here with you, or I write it at home, alone, where we’d be texting all night. Me being here is just cutting out the texting time. You do art, I do English MLA formatting.” 

“I don’t miss school,” Derek said from his architect’s desk that sat in the corner of the loft, usually covered in too many papers to do anything with. He had his sketch pad out, wearing only a grey tank top, so his arms were covered in smeared charcoal. He had a smudge on his cheek as he turned to look at Stiles, who sat on the couch, cross-legged, with his laptop in his lap. 

“Well aren’t you lucky you’re already out,” Stiles grumbled as he sifted through his MLA formatting book. “How do you cite a newspaper clipping, this is bullshit.”

“Don’t ask me, I art for a living for a reason,” Derek said as he turned back towards his work. Stiles cracked a smile as he found the page he needed. 

It was a normal Wednesday night. Well, semi-normal. Derek didn’t work most Wednesdays, so he had the day to himself until Stiles got out of school. After lacrosse practice, Stiles came over, freshly showered. Most of the time they fucked, well, Stiles fucked Derek. They still hadn’t gotten Stiles up to the size plug that Derek insisted Stiles be able to take comfortably. 

Comfort. Derek was all about comfort, about making sure Stiles was okay with what they did. Stiles understood why, but sometimes he just wanted to get it over with, to take him. When he got overly eager in bed, Derek usually stopped what they were doing as Stiles squirmed beneath him, wanting more. 

“There’s no rush,” Derek insisted, every time. Stiles groaned thinking about it, how to him there was a rush. He _needed_ him. He felt an ache within him and he was pretty sure that if Derek fucked him, not with any toys, that the ache would go away. He wasn’t going to lie, sex with Derek was amazing, mind-blowing even, but the fact remained that Stiles’ body seemed to know what it was missing. 

No matter how many toys they used, Stiles knew the real thing would be ten times better. Stiles stopped typing as he stared at Derek’s ass. He wore his favorite jeans, faded and soft to the touch, barefoot as he stood hunched over the angled desk. 

“Derek,” Stiles said.

“No,” Derek said without looking up from his drawing. 

“You don’t even know what I was going to say,” Stiles said, lying down on the couch, pouting though Derek wasn’t even looking at him. “Derek,” Stiles whined. 

“We’re not fucking,” Derek said easily. Stiles grunted, unmoving as he pressed his cheek against the couch cushion. “You need to write that paper.”

“Okay, Dad,” Stiles grumbled. Derek’s head shot up at that, his muscles rippling as he turned to look at Stiles with his eyebrows raised. “That was not meant to be in a sexual way, oh my god,” Stiles said, sitting back up. “Get your mind out of the gutter, Hale.”

“You put it there,” Derek pointed out. “I’ll blow you if you finish that paper.” 

“Wow, you know how to get me motivated,” Stiles said with a sigh, but didn’t move. “Look at me, hurrying.”

“You’re a little shit,” Derek said as he ducked his head, kneading his eraser before using it. 

“Derek.”

“ _Stiles_ ,” Derek said incredulously. “You said it was due tomorrow--”

“I have a serious question,” Stiles said, sitting up. Derek’s face softened as he looked at Stiles this time. “Come here.” Stiles watched Derek comply, standing before him with coal-colored fingers, his tattoos popping in stark contrast. 

Stiles shoved his laptop onto the coffee table, putting his hands in his lap. He knew he didn’t have anything to be embarrassed about, not with Derek, and not about sex. Derek was the king of sex, in Stiles’ mind. He knew Derek had been with a lot of people, despite the fact that they didn’t talk about it. That was beside the point, though. 

Derek looked down at Stiles expectantly, so Stiles cleared his throat. 

“I was thinking about something, and I wanted to see, like...” 

“What were you thinking about?” Derek asked, squatting down in front of Stiles so they were more or less eye to eye. He reached his hand out, taking Stiles’ hand in his. 

“What if I wanted you to shave me,” Stiles said, licking his lips as he looked in Derek’s eyes. Derek’s pupils dilated visibly before Stiles’ eyes as he swallowed. “Like, do you think that would help?”

“You want me to do it?” Derek asked, his voice quiet, hoarse. Stiles nodded. 

“Yeah,” Stiles said, his throat so dry he had to so swallow as well, wetting his mouth. 

“I can do that,” Derek said, leaning in for a kiss. Stiles opened his mouth for Derek, his eyes closing as the kiss deepened. Stiles pulled Derek closer as he untangled his legs. Derek put his hands on Stiles’ thighs, sliding them up and down, beneath the running shorts Stiles had on. Stiles gasped against Derek’s lips, a whine escaping from him when Derek backed away, ending the kiss. “You need to finish your paper first.”

“Evil,” Stiles said as he chased Derek’s mouth with his own for another kiss before Derek stood up. When he did, Stiles could tell how turned on Derek was by the thought of shaving him. 

“Hurry up,” Derek said, pointing at the computer. Stiles beamed at him, happy to have the weight of the question lifted off his shoulders. He thought about doing it since he rimmed Derek, felt how smooth his ass was compared to the coarse hairs. He trimmed his own pubic hair the week before, not as close as Derek did, but he could tell that Derek liked it better, even if he hadn’t openly commented about his preference. It was Stiles’ decision, and the look in Derek’s eye when he saw that Stiles groomed himself was encouragement enough for him.

Stiles didn’t talk for the hour it took him to finish his paper.

“Done, I’m done. So done. The most done,” Stiles said as he stretched his arms upward in triumph. 

“Congrats,” Derek said as he stood up, arching his back as he stretched as well. “Food?” 

“What? No food,” Stiles complained. “You said--”

“Are you seriously turning down food?” Derek asked. 

“For sex?”

“For shaving,” Derek pointed out. “There’s a difference.”

“No sex?” Stiles asked as he scratched his belly, showing some skin as he did so. Derek noticed his ploy. 

“There will be, but later,” Derek said, looking to the clock. “It’s eight.”

“No curfew,” Stiles said in a sing-song voice. Derek snorted as he opened his fridge. 

“Help me cook,” Derek said as he took out eggs. 

“What,” Stiles said, standing up. “You want me in your kitchen?” 

“On second thought...”

Stiles walked up and playfully punched Derek in the shoulder, then kissed the same spot, his hand sliding down Derek’s back. 

“What are we making?” Stiles asked as he watched Derek take out an onion, a green bell pepper, and salsa. 

“Omelettes,” Derek said. “Their easy, fast--”

“Like me,” Stiles said with a grin. Derek laughed, his head thrown back as his body shook. Stiles rested his chin on Derek’s shoulder, pleased with himself. 

“Cut up some onion and a couple of slivers of the bell pepper for me,” Derek said as he got down a pan to cook the eggs in. 

“Sure,” Stiles said setting about in his task. Derek turned up the music, which had been on rather low as Stiles worked before. After he was done, Stiles watched Derek make their omelettes. Derek’s didn’t have cheese, but Stiles piled it on his. They ate standing up, leaning against the kitchen counter before leaving the dishes in the sink for later.

“I have onion breath now,” Stiles said as they ascended the stairs. “Can I rinse?” He asked. 

“Yeah, I’m going to brush my teeth,” Derek said. “And wash my arms, at least.” He showed Stiles his hands, greyed from working. 

“Good idea,” Stiles laughed before he swished mouthwash around in his mouth. Derek shoved at him before soaping up his hands. 

“Grab a towel, okay? Then go get undressed.” 

“Okay,” Stiles said, a happy sort of anxiousness flowing through his body. He took one of the towels Derek had folded up on a rack over the toilet, bringing it into the bedroom with him. He stripped down to his boxer briefs before he laid the towel out near the edge of the bed. 

“Okay,” Stiles said to himself as he smoothed his hands over his stomach. Derek appeared, shirtless, his jeans riding low on his hips, carrying the supplies. Stiles took a deep breath as he stepped out of his briefs. “Back or stomach?” Stiles asked. 

“Back,” Derek said after a moment of consideration. He set everything down before going back for a bowl of water to rinse the razor with. When he returned, he grabbed a pillow to put on the floor for his knees as Stiles got situated. He lifted his legs, holding them up, his flaccid dick laying against his stomach. 

Derek took a washcloth, wiping across Stiles’ ass, wetting the area, making Stiles’ dick twitch. He lifted an eyebrow at him, to which Stiles gave a shaky laugh. 

“Don’t judge,” Stiles said easily, craning his neck to look at Derek as he applied shaving cream. “Shit, that’s cold.” Derek looked like he tried not to laugh at him, but stayed quiet. Instead, he kissed the back of Stiles’ thigh. 

“Try not to move,” Derek said. Stiles rest his head against the mattress, unsure about what it would feel like. With the first pass of the razor, Stiles shivered. “Stiles.”

“Sorry, sorry, I wasn’t sure-- I’m fine,” Stiles said, gripping his legs tight behind the knee. Another pass of the razor, and Stiles felt the coolness, wet, and the weird feeling of being shaved so intimately. Stiles twitched when he felt the washcloth on him, the sound of the razor being cleaned in the water. “It’s not done, is it?” Stiles asked, unsure. Derek’s mouth turning upward was answer enough. Stiles let his legs fall, his hands dropping to his side. 

“I wasn’t done,” Derek said plainly. 

“Shit, sorry,” Stiles said, lifting them back. Derek’s hint of a smile turned into a smirk as his face disappeared. Stiles moaned as Derek licked a line up the length of his ass, to his balls. “Holy shit,” Stiles said. It felt different, way different as Derek rubbed a finger against Stiles’ hole, then delved his tongue inward. “Shit, fuck,” Stiles said as his legs shook. He squirmed, his stomach clenching as Derek ate him out, his eyes closed as he seemed to enjoy taking his time with Stiles. 

Derek’s finger teased at his opening as he kissed the inside of Stiles’ thighs, then took Stiles’ balls into his mouth, sucking on them as he circled his finger around Stiles’ opening. 

“You look so fuckable right now,” Derek said, his head leaning against Stiles’ open thigh, his finger fucking into him slowly. “I can’t wait to--”

He stopped talking in order to lick, his tongue lapping at his opening, sucking and generally driving Stiles crazy. Stiles took it upon himself to wrap a hand around his cock, stroking as Derek buried his face against Stiles’ ass, his stubble scraping against the freshly shaved skin. Stiles knew there would be pain later, stubble burn, but the scratching and the feel of Derek against him had his back arching, his toes curling. 

Derek knew how to make him feel good, end of story. 

“Fuck, Derek, I want to feel it--” 

The loss of Derek’s mouth against him was apparent as cool air replaced his warm, wet tongue. Stiles reached a hand between his legs, feeling his smooth hole, groaning as he slipped a finger in.

“Shit,” Derek said as Stiles moaned, placing the heels of his feet on Derek’s shoulders for leverage. Stiles whined as he attempted a second without lube as he jacked himself off. “Hold on,” Derek said, shifting slightly as he reached for the SILK that he kept in the bedside drawer for times such as these. “Here you go,” Derek said as he pumped it on Stiles’ fingers. 

“Fuck,” Stiles said as he pushed his fingers inward, “damn, that’s so fucking--” Stiles moved his hips, fucking himself as Derek watched. “I need... Derek, I need more.”

Derek moved, then, adding a finger along with Stiles’ two, pushing inward. It felt so good, the stretch perfect as Stiles panted for breath. “Derek,” Stiles said, his head rolling to the side as he picked up the pace with his hand, jacking himself off in a way that he knew he would come quickly. Derek added a second finger, making Stiles fucking _laugh_ at the stretch. He could handle it, but the difference in feeling was just that... laughable. 

“Why didn’t you tell me to do this sooner?” Stiles asked. 

“Your body, your choice,” Derek said, his voice calm though Stiles knew it was all fake: Derek was probably about to come in his jeans. 

“I want to try,” Stiles said. “Right now, I want to--”

Derek pulled his fingers out of Stiles’ ass, caressing Stiles’ thighs as Stiles dropped his legs, letting Derek get up. Stiles took his own fingers out, switching hands as he jacked off with his right instead of his left, holding on to the base of his dick to hopefully hold off his climax. He wanted to come from Derek fucking him. 

Stiles watched as Derek went into the bathroom, grabbing the box of condoms. 

“You should really keep those in here,” Stiles said as Derek returned, unbuttoning his jeans as he walked. 

“I never want to assume,” Derek said as he tossed the condom onto the bed beside Stiles. “Scoot up the bed, get comfortable with a pillow under your ass.” Stiles moved, grabbing the pillow he usually slept on and situated it under himself as Derek stripped down, then climbed onto the bed, taking Stiles’ face in his hands as he kissed him. Stiles licked into Derek’s mouth, pulling him close as Derek spread Stiles’ legs with his own. 

“Are you sure?” Derek asked, his thumbs caressing Stiles’ cheeks. Stiles nodded his head as he bit down on Derek’s lower lip, sucking on it. 

“I want to try,” Stiles said as he rested his head back against a pillow. The sound of Derek opening a condom brought Stiles to reality. Derek was about to fuck him, finally. 

“You let me know if you want to stop,” Derek said as Stiles watched him roll the condom on. He looked bigger, so much bigger than one finger, two, or three. Stiles nodded his head. 

“I promise,” Stiles told him, his hands coming up to hold onto Derek’s shoulders. Derek lined himself up to Stiles, and Stiles could feel him as he pressed in slowly. Derek moaned as he looked down at his cock, watching as he moved his hips. Stiles knew he was barely in, barely breaching him, but he couldn’t help but gasp at the stretch of him. Derek stilled as Stiles gripped him tighter. “Keep going, don’t stop.” 

Derek rocked back and forth again, sinking in deeper. “Fuck, fuck,” Stiles said, his body instinctively moving away from Derek. The slide was easy, but the size of him made Stiles’ body shake. Derek moved against him, fucking him shallowly, his mouth on Stiles’ shoulder, leaving a trail of open-mouthed kisses along his neck line. 

“Stiles,” Derek said, his voice a broken moan against his lips. Stiles moaned, his mouth open as Derek slid in deeper, filling him up like no plug, no toy could. Stiles grunted as he moved against him, wanting to try for more. 

“Fuck, fuck,” Stiles shouted, his fingers raking down Derek’s back. “Please, please, I can’t--”

Not even a second later, Derek is pulling out of him, the loss of his cock leaving him feeling empty. “Shit.”

Derek’s hand replaced his cock, fingers pressing against Stiles’ opening, but not inward. Stiles clenched his ass, attempting to close the gaping hole as Derek’s teeth raked across his shoulder. 

“You did so well,” Derek said, his lips brushing across Stiles’ skin. Stiles wrapped his legs around Derek’s waist, keeping him close. Derek placed his hands on Stiles’ hips, grinding his hips against Stiles’, his cock sliding against Stiles’ own erection. Stiles found Derek’s mouth with his as he moved against Derek, rolling his hips as they rutted against each other. “You’re so close.”

“I’m sorry,” Stiles said, unable to help himself. “I couldn’t--”

“Next time,” Derek said, kissing Stiles’ cheek, then his earlobe, his tongue lapping at it before he nipped playfully. “Right now, I’m gonna make you come.” 

“Okay,” Stiles said, his voice shaking. As Derek took both of them in his hand, Stiles moaned. “Fuck, Derek, I need you.”

“I’m here,” Derek promised. “I’ve got you.” Stiles laughed, his hands in Derek’s hair as he came between them. Derek, too, stilled over him, coming into the condom. 

Stiles lay there, his body throbbing, legs like jelly as he let them fall to the side. Derek rolled off of him, bringing a pillow close as he stared at Stiles with one eye, glasses crooked as he lay there. Stiles shifted in place, draping a leg over Derek’s as he placed a hand on Derek’s stomach. 

“I wish I could stay,” Stiles said, his nose pressed against Derek’s shoulder. 

“School’s a bitch,” Derek said with a sigh, his eyes closing. 

“You working doubles all weekend?”

“Yeah,” Derek said, his voice hollow. Stiles quieted, the feeling of drying come making him feel disgusting. 

“I should clean up and head home.” He sat up, wincing as he moved. Derek sat up, too, his hand on Stiles’ thigh. 

“Hey, you know you can talk to me, right?” Derek asked. Stiles nodded his head as he got up, leaving Derek on the bed. He didn’t know what his problem was, really. Derek told him he wasn’t ready, but he wanted to try. He tried, he did, but he wasn’t ready. 

As he washed himself off, Derek appeared in the doorway wearing a pair of loose fitting sweats. Stiles avoided his gaze as he washed his hands, feeling very naked in front of him. 

“You can stay, if you want,” Derek said. 

“You know I can’t,” Stiles said as he leaned against the counter. 

“The offer is still there.” 

“I’m sorry,” Stiles said, finally looking up at Derek through the mirror. Derek’s shoulders sagged as he stepped forward, wrapping his arms around Stiles, turning him around. 

“You know how I feel,” Derek said, his hand low on Stiles’ back. “I want you to be comfortable, I don’t need to fuck you to get off--”

“I know, I just... I wanted it, but I’m not-- I couldn’t do it,” Stiles said against Derek’s neck.   
“I feel like I should be able to.” 

“We’ll work on it,” Derek said as if it was that easy. “We’re working on it.” 

“Yeah.”

“Don’t worry about it,” Derek said, kissing him. “Until you’re ready I think I can keep us occupied.” Stiles grinned. 

“I know you can.”


	9. Chapter 9

So they had a routine, no big deal. Derek worked at the store and the gallery most days while Stiles went to school and lacrosse practice. They texted, mostly during Stiles’ English class, throughout the days and for the first time since Derek could recall, that didn’t bug him. 

It wasn’t clingy in a way that put him off because he was the one instigating most of the time when the store was slow during the day. Stiles always responded within minutes, unless he was in the middle of a test. But usually Derek knew when those were. 

It was like they were dating. Which they weren’t, not really. There wasn’t a label stamped on their foreheads, or no Facebook for that matter. Actually, they weren’t Facebook friends. Stiles hadn’t even mentioned it, which told Derek all he needed to know. He didn’t need the label, riding the casual relationship train for a number of years. It did surprise him, though, that Stiles hadn’t brought it up. 

Labels weren’t a thing. 

At least, they weren’t until they were out watching the newest Wes Anderson movie on a Friday night and ran into Stiles’ best friend Scott and his girlfriend, Kira, the same girl from the gallery all those months before. 

“Scott, this is my-- Derek,” Stiles said by way of introduction. Derek didn’t react to it as he stuck his hand out. He let Scott gawk at his tattoos before taking his hand back. “Derek, this is Scotty and Kira.”

“Nice to meet you, finally,” Derek said to Kira. She beamed at him. 

“Likewise. Are you guys seeing Budapest Hotel?” She asked. 

“Yep, Derek loves Wes Anderson,” Stiles supplied. It was true, Derek admitted to it weeks prior when they had a marathon of _Moonrise Kingdom_ , _Rushmore_ , and _The Royal Tenenbaums_. Having Stiles state it without thinking had Derek smirking. Sort of like how Derek knew that Stiles liked Christopher Nolan a lot. He blamed Batman. 

“Sweet, you guys should sit with us,” Scott said. Derek said nothing as he slipped his hands into his back pocket, letting Stiles decide. Stiles didn’t even glance at Derek as he clapped Scott on the shoulder. 

“Sounds awesome, bro.” 

They stood in line for tickets, letting Scott and Kira go first. Derek watched as Scott paid for Kira’s ticket, her face as she smiled at him. Derek took out his wallet, taking a deep breath as he stepped forward. 

“Two for Grand Budapest,” Derek said, slipping his card to the teller. 

“Hey,” Stiles said, frowning. “I was gonna get mine.”

“You get the popcorn,” Derek said as he showed Stiles the tickets, covering his face with them. He leaned forward, dropping them in order to kiss him. Stiles smiled against the kiss, but took the tickets from Derek’s hand as he headed inside. 

“I’m going to get you back for that.”

“For paying for you?” Derek asked as they stood in line behind Scott and Kira. 

“Yeah,” Stiles said as Derek put a hand around Stiles’ waist. He hated PDA, really, he didn’t know what was wrong with him. Touching Stiles just seemed like the natural thing to do. “Do you just want popcorn? Or candy?”

“You know you want Reese’s Pieces,” Derek pointed out. 

Stiles grunted, his hand resting over Derek’s. 

“You know me so well.” 

Derek grinned, because it was so, so true. 

They got seats 3/4 of the way back, in the center, just where Derek preferred to sit. Scott wanted to sit in the very, very back, but Derek refused to sit in the makeout seats. He wasn’t a teen. Well, he was fucking one... that was beside the point, really. He could fuck at home, he wasn’t about to go down on Stiles in the movie theatre because they didn’t have anywhere else to get off. He kept that to himself, though. 

Stiles sat between him and Scott, and Derek was surprised at how, well, like teenagers they were together. They laughed through the previews, threw popcorn at each other, and Derek could tell they were talkers during movies. When the movie started, Derek steeled himself for tuning Stiles out, but it was unwarranted. Stiles quieted, his hand finding Derek’s, their fingers intertwining easily on Derek’s thigh. Derek was glad they went to the theatre where the arm rests moved, with the stadium seating. 

“We should double date more often,” Scott said, practically bouncing once they were out of the movie. Derek almost made a comment about a foursome he had once, but decided not to as Stiles said he’d like that. They went their separate ways in the parking lot, leaving Scott and Kira to their own devices. 

Stiles drove, since they came from Derek’s after he got off work. Once inside the Jeep, Derek let out a sigh. 

“Not big on double dates, huh?” Stiles joked as he cranked the Jeep, turning it on with a loud rumble. Derek gave a short chuckle that was more like an audible exhale as he wiped his hand over his face, rubbing under his glasses with his index finger. 

“All I can think about are foursomes,” Derek admitted. When he looked up at Stiles, his jaw was hanging wide open. 

“We aren’t doing that,” Stiles said pointedly. “Not with Scott, that’s like, crossing a line. Dick touching with my best friend is like--”

“I wasn’t suggesting that,” Derek said, laughing. “I was merely stating that double dates make me think of foursomes.” 

“Jesus,” Stiles said, shaking his head as he let out a laugh of his own. “Now I’m imagining you with four guys--”

“There were girls there too,” Derek said, his voice quieter. “We don’t need to talk about it.”

“Yeah, we do,” Stiles said earnestly. “I want to know about you,” he said with a shrug. “Like your past, what you did before the store, where you learned to draw, who you’ve been with is what makes you who you are.”

“True,” Derek said, searching Stiles’ face for something he couldn’t find: judgement. 

Stiles drove the fifteen minutes it took to get from the theatre to Derek’s loft. The radio in the Jeep was busted, so the ride was quiet, save for the sound of the engine. Derek, lost in thought, zoned out for the duration. When the Jeep came to a halt in the parking lot, Derek couldn’t remember them driving down the road at all. 

He jingled his keys in his hands as they ascended the stairs, their footsteps echoing off the walls. Stiles wasn’t normally this quiet, but Derek didn’t comment on it as he slid open the door to the loft, flipping on the lights, then depositing his keys in a bowl on the kitchen counter. 

“Are you going to tell me?” Stiles asked, standing in the doorway. “Or are you going to deflect again?”

“I didn’t realize you wanted me to,” Derek said. He watched as Stiles shoved his hands in his jeans pockets, hunching his shoulders over, making him look smaller than Derek knew he was. “How much do you want to know?” 

“As much as you’ll tell me. Who was your first?” Stiles asked. Derek sucked in a breath, looking to the ground. 

“First girl I thought I loved was a girl named Paige,” Derek said. “She died.” 

“Oh, shit.” Stiles said, walking forward. “I’m sorry--”

“Don’t be,” Derek said, shaking his head as they hugged. “It was a long time ago. All I have now are good memories of her.” 

“You said love, like you didn’t--”

“We didn’t have sex,” Derek said. “That came later.” He knew his voice dripped with disdain, but that always happened when Derek thought of _her._ Derek exhaled, pressing his lips to Stiles’ head, his fingers carding through his hair, longer now, no longer buzzed short. “I was sixteen, she was in her twenties.” Stiles held his breath, clinging to Derek. “I didn’t know what I was doing.”

“What happened?” Stiles asked, his voice cracking. 

Derek shut his eyes, wanting more than anything for Stiles to understand that what they had was nothing like anything he had with Kate. This was _different_. She stole everything from him, whereas he hoped he was _giving_ everything to Stiles. 

“She broke me, made me feel like shit. I thought I wanted it, you see. I thought that was what BDSM was. It’s not. Sex should be enjoyable, for all parties involved.” Stiles was quiet, his fingers clutching Derek’s shirt. “After she left me, I just... slept with a lot of people. I didn’t care who they were.” 

“The store?”

“Yeah, the store,” Derek said. “But I was still young then. Nothing like I am now. I’m mellower, now, comparatively. I learned a lot there, and then one day I met Jen.” 

“Jen?” Stiles asked, his head lifting. 

“She was my last relationship, four years ago now.”

“Four years ago I was--”

“Don’t remind me,” Derek said, his hand rubbing circles on Stiles’ back. “That’s that. That’s me.”

“What happened?” 

“We broke up,” Derek said with finality. “It’s what people do.” There it was, on a silver platter. Derek didn’t date, he hadn’t dated in years. Stiles was in his bed more often than any other since that time, but they weren’t in a relationship. Derek dropped his arms, deciding he was too close. He needed air. 

“I dated this girl, Heather,” Stiles said, filling the heavy silence. “We made out some, she let me feel her up, you know, but nothing more,” Stiles said as he scratched his head. “She doesn’t even go to my school, we were childhood friends. No one I go to school with will touch me with a ten-foot pole.”

“Well, high school is full of dumbasses that don’t know anything.”

“Hey,” Stiles said, offended. 

“Sorry, but it’s true,” Derek said as he walked towards the spiral staircase. “Want to come up?” Stiles hesitated, which had Derek stopping with his hand on on the railing. 

“I don’t-- am I, are we--?” Derek swallowed, his gut sinking. Stiles wanted the label, he needed it. He wanted to know what he was to Derek. 

“We’re what you want us to be,” Derek said, meaning it. 

“Are you fucking other people?” Stiles asked in a rush. Derek’s eyes widened. He wasn’t, no. He hadn’t since before Stiles walked into his life. 

“No, are you still streaming?” Derek asked. Stiles bit his lip, looking to the ground as he nodded his head. “Hey, don’t-- that’s okay, you know, if you do stream. I was just wondering.”

“I’ll stop if you want me to,” Stiles said as Derek descended the three steps he managed to go up before he stopped. 

“No, I’m not giving you any sort of ultimatum,” Derek said as he put a hand to Stiles’ neck, squeezing it reassuringly. “You do it if you like it.” 

“I can’t do it then say I don’t want you fucking other people, that’s just--”

“Not even the same thing,” Derek said. “Besides, you’re not fucking anyone but yourself on those, right?” 

“Right,” Stiles said, looking Derek in the eye. “Just myself.”

“Then no problem,” Derek said as he leaned in for a kiss. Stiles met him, his lips reaching out, wet and open for him. Stiles clung to him, his hands holding tight to Derek’s waist as the kiss deepened. “Stay.”

“I promised Dad I’d be home tonight,” Stiles said. “But I didn’t say when.” Derek grinned against Stiles’ open mouth, his tongue delving inward as he held the back of Stiles’ head. 

“So we have time?” Derek asked. 

“Yeah,” Stiles said after a moment. 

“Unless you don’t want to fuck me,” Derek said. “We don’t have to every time we are together.”

“I like fucking you,” Stiles said, his fingers hooking in Derek’s belt loops. “But what if we just... I want to make out?”

“We can make out.”

“You denied me making out at the movies,” Stiles joked. 

Derek rolled his eyes as he kissed Stiles, enveloping him in a hug as it deepened. 

-

“Stiles, stop playing with the radio and pick a station,” Derek said as he swatted Stiles’ hand away. “Or put your own music on.” 

They were on their way out of Beacon Hills after Derek picked Stiles up for the day. Derek managed a Saturday off, and he planned on taking Stiles to a ranch on the outskirts of Beacon County. Stiles fidgeted beside him, distracting him enough that he wasn’t watching the speed limit change as they approached a sparsely populated area. 

It didn’t take long for Derek to see flashing lights in his rearview. 

“Shit,” Derek said as he pulled over, exhaling out his frustration as he reached for his glove box in order to get his registration card. He was bent over Stiles’ lap when an officer knocked on the window. 

“Fuck,” Stiles said as Derek rolled down the window. “Dad.”

Derek’s stomach plummeted when he realized that the sheriff before him was Stiles’ father. Sheriff Stilinski stood there, bent over so he could look into the car, with his hand on his gun. 

“Son,” he said, pained. Derek held out his license and registration, which the sheriff took without comment to him. Eventually, he looked Derek in the eye. “You’re Derek?”

“Yes, sir,” Derek said, knowing full well what that tone meant. The sheriff looked at Derek, then at Stiles. 

“Please step out of the vehicle.”

“Dad, you can’t--”

“Please,” he said, his voice firm as he took a step back from the car. Derek unbuckled his seatbelt without a word, getting out of the car as Stiles scrambled to follow, practically running around the car. 

“Stiles, I want to speak with Derek for a moment,” he said, his gaze not leaving Derek’s.

“Dad, you can’t kill him,” Stiles said, clearly distraught. Derek’s chest tightened, because the sheriff’s hand was still on his gun, though it was holstered. 

“I’m not going to kill him, Przemysław, now give me a minute.” Stiles stepped back at the usage of his first name, that Derek had seen on his driver’s license multiple times but had never heard it aloud and had no idea what it sounded like. He probably couldn’t pronounce it again if a gun was put up to his head. 

Once Stiles was back in the car with the door shut and the windows rolled up, the sheriff looked Derek over, his eyes stopping on his tattoos. 

“You’re dating my son.” It was a statement more than a question. Derek held his tongue before he said they weren’t dating. He wasn’t about to explain their label-less relationship to an armed father. 

“Yes, sir,” Derek said. He tapped the driver’s license against his palm, looking down at it, presumably at Derek’s birthdate. 

“You do realize my son is in high school, right?” He asked, giving Derek a look that he wasn’t sure he could describe. Like he wanted to make sure Derek knew, in case he was being _lied to_. 

“Yes, sir.” Derek was fully aware that he hadn’t said two words besides those, but he didn’t want to step out of line. 

“Do you know Deputy Parrish?” He asked, which threw Derek off. 

“He’s my best friend, actually,” Derek stated. 

“Huh,” he said, looking Derek over once more. The car door opened, getting both of their attention as Stiles’ head popped into view. “Back in the car.”

“Dad--” The sheriff sighed, sounding a lot like Stiles as he did it, his hand on his hip instead of on the gun. “Don’t give him a ticket.”

“He was doing fifteen over,” the sheriff said, pointing the registration and license at Stiles. “And you are getting in my cruiser.”

“No,” Stiles said, standing up with his hands on the top of the Camaro. “We were going horseback riding, Dad. We’ve been together for months. You promised privacy--”

“And I said open line of communication,” he said, sounding more hurt than anything. He handed Derek back his information, stepping towards the car. “So you’re grounded.” He turned to Derek. “He’s grounded for two weeks. Don’t call or text him, I’ll have his phone.” Derek nodded as he watched Stiles hand it over, looking over his shoulder as he walked to the cruiser. His dad made him get into the back, even. 

Harsh. 

Once stowed away, the sheriff walked back over to Derek. 

“I’m letting you off on a warning,” he said, though Derek wasn’t sure if he meant about speeding or Stiles. He leaned in closer, his eyes narrowing. “I don’t know what you’d want with a teenager, Derek, but maybe you should spend the next few weeks rethinking what you’re getting out of dating my son.” 

“Okay,” Derek said, shocked at his tone. It wasn’t berating or angry, but honest. 

“Two weeks,” he said as he walked towards the cruiser. Stiles had his arms crossed as Derek watched them pull away. 

-

 

Derek didn’t realize how often he talked to Stiles until suddenly he wasn’t there. No texts, no phone calls, no anything. 

His apartment seemed empty without Stiles in it, so he spent his free time at Laura’s, or Kyle’s. He went to the city over the weekend, to the bar. He hadn’t been out in months, really, spending most of his time with Stiles. There was still another week left of Stiles’ exile, and Derek definitely felt the distance. 

After a few beers, he wanted contact. Well, what he wanted was Stiles, but there wasn’t a Stiles nearby, or within reach, really. With a full body buzz happening, Derek let himself be flirted with. He leaned on the bar, grinning as some guy with a crooked smile bought him another beer. He wasn’t half bad, with nice arms and an angular jaw, but Derek knew it wasn’t going anywhere. 

He and Stiles talked about fucking other people: they weren’t doing it. 

This guy was coming onto Derek pretty hard, though, and Derek would be lying if he said he wasn’t interested. His life before Stiles was uncomplicated, with him bedding anyone he wanted. He wanted Stiles, he knew he did, he _liked_ Stiles, but he hadn’t gotten to talk to him before he got into the cruiser. 

What if Stiles changed his mind, or didn’t think Derek was worth the trouble that came with dating an older person. Derek drained his beer then smirked at the guy sizing him up. 

“Want to get out of here?” They asked him. Derek’s body tingled as he hesitated. 

“I’m gonna pass,” he said, shaking his head as he tapped his fingers idly against the bar. The guy’s ass was tight, slappable even, as he walked away rejected. Derek bit his lip, looking up at the ceiling. 

He walked outside to get air, automatically reaching for his phone and dialing Stiles’ number. It rang once before it disconnected. 

“Fuck,” Derek said, frustrated as he carded his fingers through his hair. He couldn’t even leave a message. He tried again, against his better judgement. 

“Son, I know you don’t mean to be calling this number.” It was the sheriff’s voice over the line, sounding restrained. In his drunken haze, Derek bit his lip as he leaned against the brick building. 

“I’m serious about my relationship with your son,” Derek said. “I care about him, for him, sir, and I think that he knows what he wants.” 

“He _thinks_ he knows,” the sheriff said. “You do realize it’s 12:30 in the morning, right? And you’re calling me drunk.”

“I had that talk with him,” Derek said, sighing. “I had that talk, because I didn’t think he knew, or realized what he wanted, but he does. He knows, and I can’t-- I don’t want to deny him that. He said if not me, then someone else, and I’d rather it be me,” Derek confessed. 

“Why you?”

“Because I won’t treat him like shit. He’s worth more than to be used or thrown away like a toy.” 

“So he isn’t like that, for you?”

“No, fuck, I can’t even go a week without talking to him. He got under my skin, you know? I didn’t know what I needed in my life until he walked into it with his incessant questions and his smirk--”

Derek stopped talking in order to look down at his shoes. He sighed again, wishing he wasn’t so damn tipsy. He heard movement, then a knock on a door. 

“Here, son,” the sheriff said, voice muffled. After some rustling around on the other end, Derek recognized a faint ‘Is it Scott?’. 

“Hello?” Stiles asked. 

“Hey,” Derek said, smiling to himself. 

“Derek, oh my god,” Stiles said. “It says the call is already, like, ten minutes long, what--”

“I think you’re not grounded anymore,” Derek said. 

“What did you tell him? He’s been so-- He usually caves but he didn’t. I’m really sorry--”

“I told him I cared about you,” Derek said, quieting Stiles. 

“And he handed me the phone?” Stiles asked. 

“Looks like it,” Derek said. “I missed you.”

“Oh god, you have no idea how much I’ve missed you. It’s kind of embarrassing.” Derek smiled warmly, thinking about Stiles sitting on his bed in a t-shirt and boxers. “Where are you?”

“San Francisco,” Derek said, exhaling. “Outside a gay bar.”

“Cruising?” Stiles asked, his voice quiet. 

“Shot someone down, actually,” Derek said as he toed at the gravel surrounding him. “I’m kind of attached to someone.” Stiles laughed at that, which defused the tension. “I meant what I told your dad.”

“I want to know what you said,” Stiles said over the line.

“You’re going to have to ask him,” Derek stated. “He just wanted to protect you.”

“From what?” Stiles asked. “Learning things? Being with people?”

“No, he didn’t want you to be used like I was. He cares about you, and you shouldn’t be angry with him for that,” Derek said, knowing the alcohol was talking. He wouldn’t normally say something like that so openly. 

“Oh,” Stiles said, obviously taking what Derek said seriously. “Well, can I see you? Tomorrow. I want to see you.”

“Of course,” Derek said. “Come by the store if you want.”

“No, no, not in public,” Stiles said. “I-- I’ve had a lot of time to myself, being grounded and all. I couldn’t even go to Scott’s.”

“I’m sorry,” Derek said, knowing that must suck. 

“It’s not your fault, well, not really at least. But that’s not what I was trying to say,” Stiles said, stumbling over his words. “I, uh, well. You remember the first day we met?”

“Yep,” Derek said. 

“Well, I talked about this dildo I have--” Derek groaned, his eyes shutting as he placed his hand over his face. The nine-inch dildo that Derek said Stiles needed to work up to, the one that was closer to his size. “Well, I did it. And like, I really, really need to see you.”

“You used it?” Derek asked, his voice completely shot as it caught in his throat. 

“Yeah,” Stiles said. Derek could tell that he grinned. “Like, three times.”

“Fuck,” Derek said. “You know how to give me blue balls.” 

“So, tomorrow?” Stiles asked. 

“My place,” Derek said. “I get off work at seven.” 

“I’ll be there.” 

When Derek ended the call, he stood there, staring down at his phone as he thought about Stiles working himself open, perhaps on a stream, using the dildo. He groaned to himself as he pocketed the phone, beginning to walk down the street towards a cheap motel where he could sleep off his drunkenness so he could drive back in time for his shift.


	10. Chapter 10

**Notes for the Chapter:**

> only one more chapter left ;;

After what was the single most embarrassing conversation he had ever had with his father, Stiles practically ran out of the house with the keys to his Jeep. His father stood at the door with his arms crossed, looking fairly unhappy despite the ‘good talk’ he said they just had. 

Stiles, though mortified that his father knew exactly what he and Derek had been up to, felt relieved now that he didn’t have to hide who Derek was. Telling his father that yes, they have had sex, but no he hadn’t been on the receiving end was definitely something he would never forget. 

At least he hadn’t had to explain the fact that he was fucking himself on camera for money. That wouldn’t have gone over nearly as well. His father made him call the doctor’s office to set up an appointment to get himself tested, which was also embarrassing, but it seemed to put his father more at ease. No one ever told him just how, well, real life everything was. Tests, cleaning, shaving, prepping-- sex wasn’t just stick it in and go, it was complicated. 

Stiles knew that his father wanted what was best for him, that he didn’t want Stiles with someone older because of the very same scenario that happened to Derek, only Stiles knew it wouldn’t be like that for him. Derek wouldn’t turn around and do the same thing to him that happened to Derek. Besides, technically they have already had sex. Stiles hadn’t lasted long when he bottomed, he hadn’t been ready, but now he was. He was so ready. He even masturabated that morning, opening himself up again so he wouldn’t have to be prepped as thoroughly. 

He left the house early, getting to Derek’s loft fifteen minutes before Derek was even due to get off the clock. He sat in his Jeep, his leg bouncing up and down as he watched the clock. At five past seven, Stiles saw Derek pull into the parking lot. He got out of his car, running over to Derek’s driver side door. He wrapped his arms around him, breathing him in as he buried his face against Derek’s neck. 

“You smell amazing,” Stiles said, his fingers clenched around the fabric of Derek’s henley. 

“I smell like work,” Derek said, though his own face was shoved against Stiles’ neck as well, his lips pressed against his skin. 

“You smell like you,” Stiles pointed out. “And I want to climb you.”

“Let’s get inside then,” Derek said, taking Stiles’ hand and not letting go as they made their way up to his loft. As soon as the door shut behind them, Stiles pulled Derek towards him, their lips crashing together. Stiles moaned against Derek’s mouth. After being separated for so long, Derek’s arms wrapped around him had him reeling, the mere taste of him sending Stiles into a frenzy. He needed more, fast. Stiles managed to rid Derek of his shirt, his fingers fumbling with his belt as Derek walked them both towards the couch, their kiss continuing throughout. 

Stiles bit down on Derek’s lower lip as he shoved his hand down Derek’s pants, his fingers wrapping around his hardening cock. 

“God, I missed you,” Stiles said as he mouthed at Derek’s neck. Derek’s hands were all over Stiles’ back and ass, his hips. Derek’s touch was gentler than Stiles’ but just as desperate. Stiles moaned as Derek pressed his fingers against his ass, just between his cheeks, the fabric of Stiles’ jeans serving only to come between Stiles’ need to have Derek’s fingers inside him. 

“Tell me again,” Derek said as he worked Stiles’ jeans open, giving his hand room to slip beneath the fabric of Stiles’ jeans and briefs, his fingers sliding between his cheeks, pressing against his hole. “Tell me again how ready you are.” Stiles whimpered as he jerked Derek off, feeling the heat of him, the girth as he stroked. 

“I’m ready,” Stiles said as he pressed his lips to Derek’s neck. “I fucked myself this morning, to make sure.” He rutted against Derek, practically climbing him as Derek slipped a finger inward. Stiles was still slick enough that it went in easily. Derek groaned as he pressed in another, hooking them as he held Stiles close. “I couldn’t stop thinking about you, how I wanted you. I want you to fuck me,” Stiles said as he pawed at Derek’s sides, fingers leaving marks as he raked them down Derek’s back.

Stiles didn’t realize they were so close to the couch until he found himself sitting with Derek’s cock in front of his face, head swollen and wet, waiting for Stiles’ mouth to be wrapped around it. Stiles looked up at Derek as he put a hand to the back of Stiles’ head, encouragingly. Stiles stuck out his tongue, lapping at the tip of it, teasing as he fondled Derek’s balls. his fingers dragging through the finely trimmed hair at the base of his cock then upward to the dark trail of hair that led up to his chest, leading to his nipple ring. Stiles tweaked it as he took Derek into his mouth, letting it fill him up. Derek grunted, his hips canting forward as he hit the back of Stiles’ throat. 

He choked slightly, making a fist and tucking his thumb between his fingers so he could keep going. Derek taught him the trick, and he wanted to show Derek how much he learned, how good he could be. Stiles spread his own legs, letting himself cup his erection as he sunk down on Derek’s cock, letting Derek’s hand on the back of his head guide him. Derek held onto the back of his neck, sliding his cock in and out of Stiles’ stretched mouth. Stiles looked up at him though his eyes began to water. He blinked, letting the tears fall as he breathed through his nose. The heavy feel of Derek in his mouth made his own cock twitch in his grip. When Derek pulled back, allowing Stiles to draw in a deep breath, he coughed, wiping his mouth as Derek’s thumb brushed away his tears. 

“You could make me come with just your mouth,” Derek said, his tone gentle and caring. Stiles didn’t know Derek could make _him_ almost come by just talking, but he felt his stomach clenching all the same. He wrapped his thumb and index finger around his balls and base of his cock to keep from coming as he looked up at Derek again, licking his lips. He wanted to taste Derek on his lips, in his mouth. He opened his mouth, his tongue darting out. “But I think you want to be fucked.” Stiles shivered as his entire body covered itself in goosebumps. He came in his hand, thinking about Derek fucking him. 

“Shit,” Stiles gasped as his stomach spasmed, his cock pulsing as he shot out more than once, dripping down his hand and on Derek’s thigh. He leaned forward, licking it up, sucking it off of Derek’s thigh, his tongue swirling around as he did so. Derek had his hands in Stiles’ hair, now long enough that it could be grabbed onto and yanked. Derek tugged, pulling Stiles away from his thigh. Open-mouthed, Stiles chased Derek’s cock with his tongue, wanting it back in his mouth. Instead, Derek leaned over and kissed him, his tongue delving into Stiles’ mouth in order to taste him. 

“You came because you’re excited to be fucked, didn’t you?” Derek said, his lips still on Stiles’. Their position was awkward, with Stiles still sitting on the couch and Derek standing before him, his cock hanging down between his legs with his jeans still half on. Stiles still had his shirt on, even. 

“Yes,” Stiles confessed, his voice cracking as he wrapped his hand around Derek’s cock, stroking him. “I couldn’t help it.”

“Let’s get you naked and on my bed then,” Derek said as he caressed Stiles’ lip with his thumb. Before Stiles could put it in his mouth and suck, Derek stood up and began walking towards the spiral staircase, pulling his jeans up enough that he could walk without issue. Stiles shoved his jeans down his thighs as he stood up, kicking off his shoes before he made it to the staircase. He threw his shirt over the banister halfway up, then hopped over to the bed as he took off his socks. He jumped onto the bed, landing on his back as Derek walked into the bedroom from the bathroom, fully naked. 

Stiles felt himself stirring again at the sight of him, his cock impressively swinging back and forth as he walked despite its hardness. Instinctively, Stiles spread his legs as he hoisted himself up onto his elbows while he watched Derek deposit an arm full of things onto the bed next to Stiles, one of which was the larger plug. 

“I’m ready,” Stiles said. “I don’t want toys, I want you.” He didn’t want to play anymore, he didn’t want to mess around with toys or ready himself more. He knew he was ready, unlike last time. 

“I know you are,” Derek said, kissing him. “Trust me.”

“I do,” Stiles said, looking again at the toys. Derek took Stiles’ chin in his hand, bringing his gaze to Derek’s unwavering one. 

“Then you have nothing to worry about.” 

“Just you,” Stiles whispered. “I just want you.” 

“Okay,” Derek said as he kissed him chastely. Stiles hummed against the tender kiss, his thumb playing against Derek’s piercing. “What if I got one of these?” He asked. Derek groaned as Stiles tweaked it. “What if I got one on my--”

“Eight weeks no sex,” Derek said as he pushed Stiles down against the bed as he hovered over him. “None, no jacking off, nothing.” Stiles whined as he heard Derek open the lube. “Do you want it that badly?” 

“No,” Stiles panted as he held onto Derek’s biceps, then slid his hands up Derek’s shoulders to his neck as Derek spread Stiles’ legs so he could fit between them. 

“You’ve been doing yoga,” Derek said as he palmed at Stiles’ thighs, his hand brushing over Stiles’ ass. Stiles wiggled his butt, sighing as he felt the cool touch of Derek’s lubed fingers against his opening. 

“Every day,” Stiles grunted. “Grounded, remember?” 

“Oh, I remember, believe me,” Derek said as he pressed inward. “God, you weren’t lying, you’re almost ready for me even now.” Stiles couldn’t help but roll his hips as Derek fucked him with his fingers, two of them, crooked within him at just the right spot, making him drip with anticipation of what was to come. Stiles was hard again, his cock wishing to be touched. Instead, he let precome puddle on his stomach as he brought Derek down towards him, kissing him as he wrapped his legs around Derek’s thighs, fucking himself on Derek’s fingers. 

“Another one,” Stiles said as he rutted against him. Derek complied, making Stiles’ back arch as he pushed against Stiles’ movements. “Just you, okay?” Stiles said. 

“Just me,” Derek promised as he mouthed at Stiles’ neck below his earlobe. “Want to put the condom on me?”

“Yes,” Stiles said as he loosened his legs, letting them drop to the bed as Derek pulled out of him. Stiles moaned as Derek’s slicked fingers cupped his balls, rolling them before palming his cock, using the lube to stroke him, teasing at the head as he rubbed at his cock without wrapping his fingers around Stiles’ cock. 

Stiles bit his lip as he grabbed one of the condoms by him. He smiled to himself as he saw the size, XXL, and the fact that most of the time when people bought that size they were bluffing. Derek, though, was not. He stroked Derek with his left hand as he put the package between his teeth, ripping it delicately. After he rolled the condom on, he lay back down, holding onto the back of his thighs, his head against a pillow as Derek situated himself. 

“If you want me to stop--”

“I’ll tell you,” Stiles promised, though he hoped he wouldn’t have to. Derek kissed Stiles’ knee, then the other one as he gripped his cock, guiding it towards Stiles’ opening as he held onto Stiles’ waist with his other hand, his thumb rubbing back and forth as he pressed the head inward. Stiles squirmed at the intensity as he filled him, the stretch making his mouth open in a not so silent moan. Derek slid in farther, then pulled out only to do the same movement again, rocking in and out of him shallowly. Whereas before, when this was as far as they got, this time it didn’t feel as unconquerable. The feel of Derek was still overwhelming as he pushed himself in farther, but it didn’t make Stiles try to back away from him. Only now he moved against Derek, shouting out a gasp as he gripped Derek’s shoulders, biting his lip as he extended his neck with each thrust. 

“Fuck, fuck yes,” Stiles groaned as Derek moved fluidly against him, thrusting in and out expertly. Nothing about his movements were jerky or awkward, like when Stiles fucked him. Instead, these were smooth, his hands on Stiles as he hovered over him, a hand slipping beneath Stiles’ neck as he kissed him. Stiles moaned against Derek’s mouth with each thrust, which went deeper each time, harder as Stiles opened up for him. 

“How does it feel?” Derek asked him, his nose nudged against Stiles’ neckline as he held on to Derek’s ass. They were so close, their bodies pressed together as Derek rocked back and forth within him, not pulling out. Stiles gasped, his eyes open wide at the thought of Derek being fully inside him. Derek bucked his hips, changing his angle slightly, making Stiles shout as he slid against his prostate. 

“So good,” Stiles keened. “Fuck, you feel so good.” Derek moaned as he bit down on Stiles’ shoulder, his tongue laving at the spot afterwards. “The pressure, I can’t--” 

Derek began to pull out of him, but Stiles scrambled, his legs hooking around Derek’s thighs to hold him in place. 

“Don’t pull out, I just, it’s overwhelming.”

“We’re going to try a different position,” Derek said, ducking his head in order to look Stiles in the eye. “Okay?” Stiles’ grip on him loosened, letting Derek pull out of him. The loss was immediately apparent, his ass no longer full and stretched. He whined as Derek manhandled him onto his stomach, his ass sticking up in the air. Stiles buried his face in the sheets as Derek reentered him, making him shout. 

“Fuck, fuck, okay,” Stiles cried out as Derek held onto his hips, fucking into him, his pace picking up. With each thrust, Derek hit that sweet spot, making Stiles’ entire body shake. “Fuck, fuck.” Stiles moaned, unable to stop from doing so with each movement Derek made. He managed to wrap his hand around his cock, stroking inexpertly as he attempted to time it with Derek’s thrusts. He reached back, placing his hand between his ass and Derek’s pelvis, feeling him. When he felt Derek’s length, how he wasn’t all the way inside of him, Stiles groaned. “Slow down,” Stiles said. “I want you to go in all the way.” 

“Stiles--”

Derek’s voice was broken, restrained as he slowed his thrusts, pushing in deeper. Stiles swore that he could feel himself being stretched open, that he could feel Derek’s cock in his throat. He knew that wasn’t really the case, but as Derek shoved his cock fully into him, his balls against Stiles’ ass as he bottomed out, Stiles had trouble breathing. 

“You can fuck me,” Stiles said as he covered Derek’s hand with his own. “Do it.” Instead of movement, he felt Derek’s mouth on his spine, leaving open-mouthed kisses as he wrapped his hands around Stiles’ middle. Stiles yelped as Derek picked him up, taking all of Stiles’ weight as he sat down in an armchair by the bed. Stiles groaned as he sat in Derek’s lap, his legs on the ground. 

“You can fuck yourself on me,” Derek said, his voice lower than it normally was, a hand on Stiles’ stomach as the other played with a nipple, pinching it as he mouthed at Stiles’ shoulder. Stiles shut his eyes as he held onto Derek’s thighs. He rolled his hips, bouncing slightly on Derek’s cock. 

“Fuck, you’re so fucking big,” Stiles moaned as he pressed upward on his heels, then sunk back down again. This time when he went up, he let himself slide completely off of Derek’s cock, just to see how close to standing he’d get. He whined as Derek’s cock fell back onto his stomach, leaving Stiles feel empty. Derek took his cock, realigning it so that Stiles could sink back down, making him moan as he did so. “God.” 

“You feel so good,” Derek said, dazed. Stiles craned his neck so he could look down on him, his pupils completely blown so he couldn’t see but a sliver of color against black pupils. “How do you feel?”

“So full,” Stiles said, his voice coming out as more of a whine than anything else. “Stretched, thoroughly fucked.” Derek hummed beneath him as he wrapped a hand around Stiles’ cock. 

“I want you to fuck up into my hand and fuck yourself on my cock.” Stiles shuddered as he held onto the armrests. He let his head hang back, his mouth open as he moved his hips, fucking himself on Derek’ cock as he also fucked up into Derek’s still hand. Derek situated him on an angle, moving him slightly so that he lifted one of Stiles’ legs over the side of the chair. Stiles, instead, held onto the back of the chair as Derek ducked his head forward, underneath Stiles’ arm, so he could mouth at Stiles’ nipple. He raked his teeth across it, his tongue lapping at it as Stiles moved. Derek’s hand stayed still, making Stiles work for his orgasm. 

As soon as Derek’s mouth moved from Stiles’ nipple to his underarm, Stiles’ pace quickened. Derek licked and mouthed at his armpit, breathing him in as Stiles shouted, sinking down on him as he came. Derek ran his fingers over Stiles’ stomach, smearing the mess. 

“I’m going to fuck you now,” Derek said, as if he hadn’t been doing that already. Stiles groaned as Derek put both hands on his hips, holding on to his waist as Stiles put both feet on the floor to steady himself despite his orgasm-addled brain short circuiting for the time being. As Derek moved beneath him, fucking upward, Stiles shouted, his head hanging down between his shoulders as he watched Derek move. 

“Fuck, Derek, oh god,” Stiles whined as he felt each movement. Derek stilled within him, then rolled his hips slowly, riding out his own climax. Stiles panted as Derek licked a spot on his back, dripping with sweat. He was exhausted, his throat dry, his legs shaking as Derek forced Stiles to stand in order to pull out of him. Stiles looked down at Derek’s softening cock, the condom full. 

They had sex, and not _just_ sex, but Stiles was _fucked_ , finally. He watched as Derek pulled off the condom, tie it off, then put it in the trash can by the chair, like its purpose was for easy condom disposal. Derek reached for Stiles’ hand pulling him back into his lap. They were really too big to both be on the chair, but Stiles didn’t care as he put his legs over one side of it, his head pressing against Derek’s as he felt him wrap his arms around Stiles’ waist, kissing his shoulder. He was sleepy, he was sore, and most of all, he knew that Derek would take care of him. 

They got in bed, lying on top of the sheets, limbs tangled as they rested. Stiles had his eyes closed, his hand moving lazily over Derek’s as he traced invisible lines over Stiles’ thigh. When Stiles moved, he winced, the endorphins that kept the pain at bay during sex subsiding. 

When the bed dipped as Derek got out of it, Stiles rolled over to watch him pull on a pair of sweatpants. 

“Where are you going?” He croaked, his throat dry. 

“Getting us water,” Derek said. “And some Ibuprofen for you.”

“I’m fine,” Stiles said lamely. He didn’t want Derek to know how sore he was. Derek didn’t say anything as he walked towards the stairs. Stiles watched his ass as he went, the sweatpants showing it off nicely, along with his tattoos. Stiles lay there, unmoving, as Derek got them water downstairs. He could hear it, each movement, from the loft above. Derek getting two glasses directly out of the dishwasher, the ice as it came out of the freezer and into the glasses, water filling up the glasses. 

Stiles drifted off somewhere between Derek answering a phone call and him sitting back down on the bed, his hand in Stiles’ hair. Stiles opened his eyes slowly, blinking away their heaviness. 

“Drink this,” Derek said as he held a glass up to Stiles’ mouth with a straw in it so he didn’t have to sit up. Stiles did as he was told, which made him shiver. Derek knew how to take care of him. “I have medicine for you, do you want it?”

“Yes,” Stiles admitted, his face reddening. He moved his legs, attempting to stretch. He groaned as he sat up. “Please.” Derek handed him the small pills. He took them, then drank down the rest of his water, taking the straw out of the glass so he could gulp it down. 

“Who was on the phone?” Stiles asked. 

“Kyle,” Derek said as he watched Stiles drink, his eyes on Stiles’ body. “He’s off tonight, wants to hang.” 

“Oh,” Stiles said, lying back down, trying not to sound disappointed. 

“I want you to come.”

“Yeah?” Stiles asked as he curled inward, towards Derek. He was so sore, he wanted to sleep it off. Derek smiled down at him, his fingers raking through Stiles’ hair. 

“We’re going to the bar off tenth,” Derek said. “We have time to shower.” 

“That sounds so good right now, considering I have come on my stomach,” Stiles said, making a face as he ran his hand over the dried mess.” Derek snorted, getting off the bed to head into the bathroom. 

“It will help you look less like you were thoroughly fucked, too.” 

“Hey, who did the fucking?” Stiles laughed as he sat up. Walking was interesting, but as soon as he stepped underneath the spray of water, he moaned with happiness. Derek kissed him as soon as he joined him under the water. Kissing him was intoxicating, and now he knew how much he wanted Derek in his life. He had time to think while he was grounded, about Derek and their relationship. He wanted Derek to stay, wanted more than sex from him. 

Somehow they managed not to do anything but wash up in the shower. Stiles had to go throughout the apartment to find all of his clothing. His shirt had come on it, from the first time on the couch, so Derek let him borrow one. It was a henley, dark green and soft, that smelled like Derek. Stiles pushed the sleeves up to his elbows as he looked himself over in the mirror. His hair was a mess as Derek ran his fingers through it again, and the henley didn’t do a good job in covering one of Stiles’ hickeys at the base of his neck. He covered it with his hand, only to have Derek push it out of the way so he could mouth at it, looking at Stiles in the mirror. 

“You look good in that color,” Derek said as they walked down to his car. Stiles, with his hands in his back pockets, scoffed. “Or it could be because you’re in my shirt.” 

“Don’t make me come in these pants, yours won’t fit me,” Stiles said as he got into the passenger seat. 

“Challenge accepted,” Derek said with a smirk as he turned the engine over. Stiles rolled his eyes in an attempt not to smile. Sex with Derek seemed too good to be true, like they have only cracked at a small portion of what they could do together. Stiles couldn’t wait to try out more things. No matter what, he knew he could trust Derek.


	11. Chapter 11

Derek decided that he liked waking up to Stiles in his bed on Saturday mornings. After having a long, somewhat embarrassing talk with the Sheriff where Stiles told him that he could just sneak out and come over to Derek’s, he decided that Stiles could sleep over one night a weekend. Derek thought that was generous, considering Stiles had been grounded less than a month prior. There was a dinner, where Derek wore a long-sleeved button up shirt. 

It could have gone worse. 

But Stiles sleeping soundly beside Derek, his bare skin peeking out beneath the sheet that barely covered him caught Derek’s eye. He shifted where he lay nearby, scooting up to Stiles, his hand resting on Stiles’ shoulder for a moment, seeing if it woke him. When it didn’t, Derek sighed, bringing himself even closer as he breathed Stiles in. He smelled of Derek’s soap, of his sheets, and distinctly of Stiles. 

Derek was aware that the Sheriff knew they were fucking, since Stiles’ negative test results came back from the doctor’s. It was obvious why Stiles spent the night. As long as they were safe, the Sheriff said, giving them both a look. Derek supposed that Stiles was lucky, luckier than he, to have a parent that cared. Derek had Laura, but she was no role model, considering she was only a year older than him. 

He watched Stiles sleep, the rise and fall of his chest, his parted lips, the moles that dotted across his face and back. Eventually, Derek’s hand roamed down Stiles’ back, then up it once more. Stiles shifted, but didn’t wake. Derek contemplated waking Stiles up with a blowjob, but he was on his stomach, making that next to impossible. 

They were up late, going until they both fell asleep from exhaustion. Derek stretched, realizing how sore his muscles were. He could only imagine how Stiles felt after their fuck session. His hand ran over Stiles’ ass, above the sheet, before dipping down below it, his finger sliding between Stiles’ cheeks. Stiles moaned, his mouth hanging open as he slept, his legs spreading in reaction. He was still slick enough for a finger or two. Derek kissed Stiles’ shoulder as he pressed inward with a finger, feeling the wet heat of him. 

Stiles shifted, pressing back against Derek’s finger as he stretched his arms out, his eyes opening, sleep-addled. 

“Fuck,” he whispered, his voice hoarse from getting his face fucked the night before, along with shouting through Derek fucking him. “ ‘M sore,” he said as he rocked back against Derek’s finger. 

“Do you want me to stop?” Derek asked as he nipped at Stiles’ shoulder. Stiles shook his head as he panted, reaching between his legs to jack off. “What do you want?”

“Guh, can you wake me up every Saturday with your finger in my ass?” Stiles asked mid moan. Derek laughed as he pressed in a second finger, making Stiles hiss. 

“I wanted to blow you, but someone sleeps on their stomach.”

“Next time shove me, I’ll move,” Stiles said as he grunted. Derek pushed at Stiles, sending him onto his side. The sheet got shoved out of the way, kicked to the bottom of the bed as Stiles situated himself on his back so Derek could put his mouth where he wished. Derek fucked Stiles with two fingers as he took him into his mouth. Stiles moaned as he carded his fingers through Derek’s hair, tugging at it to control the pace. Derek let him, his eyes closing as he savored the taste of him. 

Stiles came quickly down his throat, the salty sweetness of him filling Derek’s mouth. When Derek pulled his fingers back, Stiles moved, straddling him, his breath stale as he breathed against Derek’s neck, then cupped his face. Morning breath and come were a mixture that he didn’t think he wanted, but as Stiles’ tongue delved into his mouth, Derek moaned. Stiles rocked his hips against Derek’s erection, a hand reaching behind him in order to wrap his fingers around Derek’s length as he moved, letting Derek’s cock slide against his cheeks. 

“God, Stiles,” Derek said as he mouthed at his neck, then his shoulder as Stiles rutted against him. “We’re going to be late.”

“Who had their fingers in my ass?” Stiles asked as he bit his lip, throwing his head back as Derek bit down, marking him, his hands on Stiles’ waist as he bucked his hips upward, meeting Stiles’ own. 

“I see my flawed plan and regret nothing,” Derek said as he lapped at Stiles’ nipple. 

“Are you going to come for me?” Stiles asked.

“If you ask nicely,” Derek said. 

“Fucking come so we can shower,” Stiles said with a smirk, getting a thrust against his entrance, making him yelp as Derek pressed Stiles’ ass cheeks together, shoving his cock between them. He was close, so close. “Come on, Derek. Come on my back,” he whispered into Derek’s ear. “Then you can lick it off me.” Derek groaned, holding tight to Stiles’ ass as he came, making a mess of Stiles’ back. He maneuvered Stiles onto his stomach, licking up his back, cleaning up every last drop. Stiles hummed happily beneath him with his eyes closed, savoring the attention that Derek paid him. 

“Come on, my sisters will be waiting.”

“Like they haven’t ever been late,” Stiles said as Derek pulled him up out of bed. 

-

Derek checked his phone for what felt like the thousandth time during his shift at the store. Working the night shift, plus it being a weekend meant that the store was busier than his normal day time stints. He was on register duty, but that didn't mean that he didn't tap his phone every so often to check for a message from Stiles; there was none. He sighed audibly, getting a look from Erica. 

"What has your panties in a knot?" Derek snorted, shaking his head at Erica's word choice. 

"They aren't in a bunch, don't you worry."

"But you are wearing panties. I knew that would be your thing."

"Thing? I don't have a thing, Erica."

"Hmm, yeah you do," Erica said as she leaned against the counter. There was a lull in customers, so Derek decided to indulge her for the time being. With a lifted eyebrow, Derek placed his elbow on the counter, then put his head in his hand. 

"I don't think panties are my thing," Derek supplied as he tapped his phone again. Still nothing from Stiles. 

"Even Stiles in panties?" Derek's mouth twitched at the thought. "We all know you like twinks, so it's gotta be something else on top of that." 

"What's your 'thing', then?" Derek asked, rather evasively.

"You know, normal stuff. Handcuffs, some nipple clamps, blindfolding," she said, leaning forward, her arm sliding across the countertop. "Looking down at Boyd as he kisses my shoes." 

Derek whistled low, but smiled. He knew she was a kinkster, but it wasn't something they normally talked about. He'd be thinking about Boyd in a whole new light next time he saw him.

"Collar?" Derek asked simply. 

"Just cuffs," Erica smiled. 

"I'm not into bondage," Derek confessed. "No ties, no blindfolds. Definitely no rope or cuffs." 

"Huh," Erica said as she tilted her head, looking Derek over. 

"What?" Derek said defensively. "I don't like being restrained." 

"Does Stiles?" Derek was almost positive that his brain short circuited. "Hello? Derek? Earth to Derek!" 

When Derek came back from some sort of mind palace about Stiles being bound, he had Erica snapping in front of his face while a customer waited for him to check them out. He handed them their change as his phone buzzed. He couldn't remember the last time he reached for his phone so quick, reading over the text. 

'No dice.' 

Derek frowned as he adjusted his glasses. Not sure what the text meant, he sent one back.

'As in no mail, or that you didn't get in?' He asked. 

"What's up? Something going on?" Erica asked, worried.

"It's Stiles," Derek told her. "He's been waiting to hear back from Berkeley and Columbia." 

"Oh wow, Columbia is in New York." Derek rolled his eyes.

"Yeah, I know that." 

"Did you tell him you want him closer?" 

"I'm not telling him how to live his life," Derek said as he got another text from Stiles. 

'No mail. Tomorrow is Sunday :(,' it read. No mail on Sunday means Stiles would be in a sour mood, deservedly, but still. 

"Maybe you should tell him--" 

"Erica, stop," Derek said, interrupting her. "I'm not making any decisions about his life for him. He's more than capable." 

"I didn't think he was incapable. I just know you, and you're self-sacrificing. He'll go off to college at fucking Columbia or Oxford or something because you hate labels."

"What? No. If he goes to Columbia it will be because he wants to. I don't have anything to do with that decision."

"Wow," Erica said. "Are you in high school?"

"No, my boyfriend is." Derek froze as he let that sink in. Erica practically bounced as Derek held his breath. "Oh." 

"Yeah," Erica said, her eyebrows lifted. "You've been fucking him for months."

"I've been fucking _him_ for one month," Derek pointed out. 

"Semantics,"Erica said with a wave of her hand. "Maybe, if you wanted him to stay, talking instead of sucking would be helpful."

"We talk." 

"The size of that hickey on your neck says you don't." 

"Hah fucking hah," Derek said as he rubbed at the aforementioned mark on his neck. His phone buzzed in his hand again. 

'Can I come over later?' 

'Sounds good,' Derek answered back immediately as he bit his lip. They really needed to talk.

-

Derek paced around his living room. He already stress wiped down his kitchen counter, and the coffee table. Stiles was late, well, later than he usually showed up. Derek checked his phone but didn't call or text him. He could wait. 

As soon as he heard the door sliding open, Derek found himself near the doorway, the anticipation killing him. Stiles' smiling face relaxed him, but Stiles' arms around him felt even better. 

"Hey to you too," Stiles said as he held him close, his fingers slipping beneath Derek's shirt. Derek sighed against him. "What's up? You okay?" Derek didn't know how to say everything that he wanted to, so he kissed Stiles instead. He opened his mouth for Derek, letting him take control. 

"Which school are you waiting to hear from?" He asked as he watched Stiles lick his lips.

"Columbia and Berkeley, you know that, though."

"I know, but which are you waiting for?" Stiles frowned at him, then took a step back. 

"Both," Stiles said, his brows drawn together. "Keeping my options open. Why? You've never asked me anything like that before." Derek shrugged, brushing off the feeling in his stomach. "Talk to me."

"Do we ever talk, really?" Derek asked, knowing he was just as much at fault as Stiles was. He should have been more communicative, not just during sex. 

"We talk--"

"About sex, sure," Derek said as he ran his fingers through his hair, tugging at it out of frustration.

"What's going on, Derek? You're freaking me out." Stiles had his arms crossed defensively and that alone made Derek feel like shit. 

"Nothing," he said. "I just--"

"Berkeley," Stiles interrupted. Derek held his breath, trying not to let hope settle in his gut at the indication. "Because I want to stay nearby."

"Stiles--"

"You told me, back when we started, that this? What we have, could be what I wanted it to be. Is that still true?"

"Yes," Derek said in an exhale of breath. He stiffened as Stiles stepped forward, cupping Derek's face with his hands. "Whatever you want it to be." Derek gulped. He could feel Stiles' breath against his skin, the warmth of his fingers as they held onto his face. 

"What I want to know is what you think we are."

Derek clenched his jaw, his eyes searching Stiles'. To him, they were serious, something he didn't allow himself to have for years. Commitment led to heartbreak, and he didn't want that for either of them. He wanted Stiles to know what else was out there. 

"I think you should go to whatever school will give you the bigger scholarship." 

"That wasn't an answer." Derek sighed, rubbing his face with his hand.

"For someone who is so fucking open about sex, you suck at speaking about feelings. Well guess what, I have feelings, Derek, for you. Having sex all the time is great, but you know what else is? Curling up on the couch and watching Marvel movies with you, marathoning Pawn Stars and every other fucking weird-ass reality show about storage wars or pawn shops that you watch. I like cooking with you, watching you cook, playing poker with your friends. We're in a _relationship_ , Derek, but the fact that you can't even say it should tell me all that I need to hear in regard to how you feel about me." Stiles shook his head, taking a step back from Derek. He caught hold of Stiles' wrist, keeping him close.

"No," Derek said as his thumb caressed the inside of Stiles' wrist. "That doesn't tell you how I feel, the fact that I can't say that. I mean, I can say it. We're in a relationship, Stiles. I like all those things too, like waking up with you in my bed, how you get my heart rate up with a single text. I can't get enough of you and that scares the shit out of me." 

"I scare the shit out of you?" 

"That's what you took from that?" Derek asked as Stiles leaned in, kissing him with a grin on his face. "But yes, you do."

"I am pretty terrifying," Stiles said, his lips pressed against Derek's, his hands slipping around Derek's waist, cupping his ass. The kiss ended as a look crossed over Stiles' face. "You were scared I would leave you."

"Yeah," Derek said, pressing his face against Stiles' neck. 

"You want me to stay."

"Yeah," Derek confessed as his arms tightened around Stiles' body. 

"Because I'm your boyfriend," Stiles singsonged, making Derek laugh. 

"Because you're my boyfriend and I'm not so sure I would be able to watch you fuck yourself in a chat with like, what? Four-hundred other guys."

"Don't be ridiculous," Stiles scoffed. "I haven't had less than seven-hundred my last two streams." Derek snorted as Stiles laughed. "Besides, I'd do a private stream for you."

"Oh, well then, that changes things." 

"For a fee, of course." 

"You piece of--" 

Stiles' body shook with the force of his laughter as it echoed off the walls of the loft. Derek couldn't get enough of it as he kissed Stiles neck, mouthing at it as he breathed in the scent of him. 

"Let's see where I get in to, okay?" 

"Okay," Derek said. He could wait and see what Stiles decided. 

-

Derek looked up as the door to the gallery opened, his entire body on edge as he saw Stiles running up to the desk with an envelope in his hand, unopened. 

"It's here," Stiles said, out of breath as he waved it around. "I ran over."

"You ran from your house?"

"No, jackass, from my car, which is parked two blocks away because everyone and their mom decided to be on Main Street at four pm on a weekday."

"You haven't opened it yet," Derek point out as he closed his sketchbook then wiped his hands on his jeans in an attempt to get rid of some of the charcoal. 

"Well, Dad is on duty and I didn't want to open it alone, so here I am," Stiles said as he bit his lip. "I wanted to open it with you." Derek looked at the envelope; it was from Columbia. Derek swallowed as he walked around to the front of the desk, giving himself time to rein in his feelings. Stiles watched him, his fingers on the envelope, waiting for Derek to get close before he opened it.

As Stiles ripped it open and read, a smile spread across his face. He bounced on his heels, then leaned towards Derek so he could read along as well. All Derek saw where the words 'you have been accepted'. 

"Oh my God," Stiles said, his eyes on Derek. "I got in." 

"I'm so proud of you," Derek heard himself say as he kissed Stiles, holding him close. Stiles clung to him, standing there in silence. All Derek could think about was the long distance, how hard it would be but that he wanted to try it. He wouldn't let go of Stiles so easily. He let his hands fall to Stiles’ waist, where he felt another envelope in his back pocket.

"What--"

"Oh, that," Stiles said with a smug face. "That's my acceptance letter to Berkeley." 

"You little shit," Derek said as he yanked the letter out of Stiles' back pocket. Stiles didn't even try to stop him as he watched Derek read over it. Derek couldn't stop himself for grinning from ear to ear: Stiles got a full ride to Berkeley.

"That's a better reaction," Stiles said without malice. When Derek looked at him over his glasses, Stiles' eyes locked with his own. "Tell me, I want to hear you say you want me to stay close." 

"I want you to stay close." Stiles grabbed hold of the back of Derek's neck, bringing him in for an open-mouthed kiss as Stiles pressed his body against Derek's. "I would do long distance, even though it would kill me. It would kill me to be that far from you, but if that's what you wanted--"

"It's not what I want. I don't want to be that far either. Different time zones? Streams? Not being able to touch you would drive me insane." Derek gasped as Stiles bit his lip, tugging at it as his fingers carded through Derek's hair. “I want to be near my boyfriend.” Derek smiled, his eyes closing at Stiles’ words. They sounded good on his lips, Derek wanted to hear more. 

“So it wasn’t just because the free ride?” Derek asked, his hands groping at Stiles’ ass. 

“I mean, that definitely helped. I’d only go to Columbia if, well-- probably a free ride.” 

“They missed out,” Derek said, kissing Stiles again. 

“Hey,” Stiles said, his fingers tugging at Derek’s hair. “Do I get a present for getting into college?” 

“Depends,” Derek grunted. “On what you want.” 

“Oh, I can think of a few things,” Stiles said, smirking. “All of which involve that swing you have in your closet.” 

-

“I know it’s in there,” Stiles said as he sat on the bed. Derek crouched down on his knees as he looked through his closet, looking for the sex swing. “I swear I saw it.”

“I haven’t used it in a while.”

“Not since we’ve been together, unless you like, curl up in it and read a book.”

“It’s not a hammock, Stiles,” Derek said, amused. He looked over at Stiles, who had lain himself out, his legs spread as he watched Derek go through his things. “Are you sure that’s what you want? That’s all?”

“All? Pfft. Please, I’ve wanted to be fucked on a swing since I saw you had the hardware hanging. Don’t deny me now.” 

“Wouldn’t dream of it,” Derek said as he sighed, leaning back on his heels. “I can’t find it though.” 

“Ugh,” Stiles said as he forced himself back, lying on the bed, pouting. 

“Hold on, let me check one more place,” Derek said as he made his way over to the bed, where he knelt beside it, looking underneath. “Aha.”

“You knew it was under there the whole time!” Stiles said, sitting up once more. 

“No, I didn’t,” Derek said as he put the large box on the bed. Stiles started opening it immediately. “Hey, hey. I have to put it together.” 

“Why aren’t you a wizard so we could just get to the fucking?” Stiles said as he snapped his fingers. 

“Because real life isn’t like that.” 

“Ugh,” Stiles groaned. 

“Why don’t you go get everything else ready?” Derek asked. Stiles rolled his eyes, but grinned as he got off the bed, kissing Derek before he walked into the bathroom. By the time Stiles walked out again, Derek had the swing up. When he turned to look at Stiles, his eyebrows rose. Stiles was naked, except for a jock strap. “Where did you get that?” Derek asked, his throat suddenly dry as he watched Stiles approach him. 

“I was wearing this earlier, you know, so I could be bent over and fucked,” Stiles said, wiggling his eyebrows suggestively. Derek couldn’t help but love Stiles’ humor, how he said things in a way that shouldn’t be sexy but made him instantly hard. “But I bought it because one of the guys on a stream suggested I wear it when I used the dildo? So my junk wouldn’t get in the way.” 

“Did it work?” Derek asked seriously. Stiles shrugged. 

“I don’t know yet, wanted you to test it out.” That definitely got Derek hard. “There’s the look I was waiting for,” Stiles said, tweaking a nipple as he leaned in for a kiss. Derek’s hands roamed Stiles’ body momentarily before finding his bare ass. Stiles got Derek’s shirt off, then managed to get his belt undone and his jeans halfway down his thighs before Derek pushed Stiles against the bedroom wall, hoisting him up. Stiles wrapped his legs around Derek as their kiss intensified. Derek couldn’t help but thrust his hips against Stiles, his fingers looping around the straps, snapping them against Stiles’ thighs, making him moan. 

“Fuck,” Stiles said as he moved against Derek. “Get your damned briefs out of the--” Derek managed to pin Stiles against the wall enough that he could shove the fabric down his thighs, freeing his cock so that it pressed against Stiles’ ass. “Yes, fuck me,” Stiles hissed as his dick slid between Stiles’ cheeks. 

Stiles was slick, ready for him. Derek stilled, confused for a moment until he realized how long Stiles had been in the bathroom as Derek readied the swing: Stiles prepped himself. 

“Condom,” Derek said as he mouthed against Stiles’ neck. 

“Check your pocket,” Stiles said with a smirk. Confused, Derek shoved his hand into his back pocket to find a condom there, waiting. “Who’s prepared? Stiles is,” he practically sang as Derek ripped the packet open. “I’m prepared. The most prepared--”

“Stop talking,” Derek said as he rolled the condom on. His legs were shaking, but he managed to do it as Stiles wiggled his ass. Derek situated himself, canting his hips upward as Stiles sank down on his cock, his mouth open in a moan. “There you go.”

“Fuck,” Stiles said as he banged his head against the wall, his fingers digging into Derek’s back as he began to move, fucking up into him. “Why are we against the wall when there is a swing?” 

“You weren’t patient,” Derek supplied as he kept fucking him. “Want me to stop?” 

“Fuck you, no,” Stiles practically shouted as Derek bottomed out. Stiles whimpered above him as he bit on his lip, his eyes shut tight as his chest heaved. “God, you feel so good.” 

“You’re still so tight,” Derek said as he bit at Stiles’ shoulder, leaving teeth marks as he held onto Stiles’ straps for leverage. “You want on that swing?” Derek asked, suddenly feeling excited about Stiles’ jock strap. It gave him something good to hold onto, it get the momentum going. Stiles would probably come untouched. 

“Yes,” Stiles said, groaning as Derek pulled out of him, letting him down onto the ground. Stiles caught himself, wobbling a little bit before he kissed Derek on the mouth, his lips open, tongue out. It was filthy, heated, and it made Derek’s dick twitch. He watched as Stiles got into the swing, his legs spread out before him. 

“You ready?” Derek asked, stepping forward. 

“Fuck yeah,” Stiles said, his voice shot as he watched Derek line himself up, his head disappearing within Stiles. Stiles moaned as the swing moved, sinking Derek deeper within him. Derek hooked his fingers around Stiles’ straps, using them as reins as he began moving, fucking Stiles. The sounds of skin slapping against skin filled the room, along with Stiles’ unwavering shouts with each thrust. He squirmed beneath Derek, panting as he looked up at him. Stiles cupped his erection, the fabric of the jock strap soaked through already with precome. Derek stilled, stopping when he was fully inside him, making Stiles shudder, his back arching. 

“Don’t touch yourself,” Derek said, moving his hips, but staying inside him. “I want to see you come without being touched.” 

“Fuck,” Stiles said as he moved, rolling his hips against Derek, making the swing move. 

“That’s good, just like that, fuck yourself on my cock. Show me what you want.” 

“I can’t-- I want you to fuck me harder, I can’t do it alone,” Stiles said as he attempted, his ankles hooking around Derek’s body, trying to fuck himself harder. “Please fuck me.” Derek slid his hands up and down Stiles’ thighs, stopping just before his groin, then going all the way to his knee and back again before he snapped the straps again. “Please.” 

When Derek started moving again, Stiles stilled, his mouth falling open. Stiles came, Derek knew, by how Stiles became limp after, pliable beneath him. Derek took the front of the strap in his hand, rubbing his palm against Stiles’ sensitive cock, making him jump. 

“Fuck, fuck,” Stiles whined as Derek hooked a finger around the damp fabric, revealing a mess of hair and come, his thumb running through it. 

“You like that?” Derek asked as he slowly moved within Stiles, picking up the pace once more. “Like how the swing works?”

“Yes,” Stiles gasped. “Why the fuck haven’t you used it on me before now?” Stiles asked as Derek felt his own climax building deep within him. His thrusts became more erratic, harder, until he held Stiles against him, stilling as he came. It was Stiles’ turn to torture Derek. He moved his hips, riding out Derek’s climax agonizingly until Derek pulled out of him. 

Stiles swung back and forth in the swing, his body limp, as Derek disposed of the condom. 

“Because,” Derek said, soon after when he helped Stiles out of the swing. “You weren’t ready to be fucked like that.” Stiles laughed as he put an arm over Derek’s shoulder to help himself walk as they made their way into the bathroom. 

“I’m glad I’m ready now because that thing isn’t coming down.” 

“You can see it from downstairs,” Derek pointed out. Stiles smiled at him knowingly. 

“Exactly.” 

Epilogue

Stiles situated himself at his desk, clicking the button that enabled his live stream. 

“Hey guys, we’re going to wait a few minutes until the chat fills up. I’m capping at two-fifty today, so if you want to chat, don’t refresh the stream. You can still watch, but you can’t type if you’re late.” 

Stiles left his computer for a minute, grabbing his bottle of water off the nightstand before returning to a few messages. He scanned the chat just to see what was being said before they got started. 

‘LET ME SEE YOUR COCK,’ one said, which wow, impatient. 

‘Where are you? That place looks different.’ 

“Wow, you’re astute,” Stiles said with a grin as he took his shirt off, looking towards the stairs. “We are in a different location today. This is actually my boyfriend’s apartment, so like the description says, you guys are going to get to watch me be fucked. Or maybe I’ll do the fucking? Who knows,” Stiles said as he waved his hand absently. “Haven’t decided. Or maybe you can decide!” 

‘Boyfriend? I bet my cock is bigger than his.’

‘Let me fuck you, I’ll show you a better time.’

‘GANGBANG PLS.’

“You guys don’t really know what’s in store here,” Stiles said with a laugh. “Believe me, he’s going to fill me up if he’d come up here!” Stiles shouted, standing up to give the viewers an eye full of his briefs. 

“Coming,” Derek called out from the bottom of the stairs. Apparently he had been on his way already. 

“Okay, guys, now’s the time to tell me your suggestions before we get started.” Stiles cast the chatbox a furtive glance before he looked up at Derek, who was still fully dressed. He grinned as Derek stepped into the camera’s view. “Come here,” Stiles said as he tugged on Derek’s shirt, bringing him close enough so that Stiles could kiss him, his other hand snaking up Derek’s shirt until Stiles broke the kiss in order to rid him of it. “I want you to help me with this chat.” They discussed this, about what Stiles wanted, about Derek fucking him on a stream. 

He got so many offers, so many people who wanted to fuck him, or watch him be fucked, that he didn’t want to disappoint, but he didn’t want to be with anyone else, either. Derek didn’t even need to be talked into it before he said he would do it. 

“Sure thing,” Derek said as he looked at the chat box. “I see ‘show us your junk’.” 

“Whose junk?” Stiles asked. “His?” He pointed at Derek, his hand teasing at Derek’s stomach, the hair there that led down beneath his jeans. “They want to see your monster cock.” 

“So show them,” Derek said with a thin lipped grin. Derek had his hand on the back of Stiles’ head already in anticipation of what was to come as Stiles undid the top button of his low-hanging jeans. Stiles knew Derek was watching the chat box as he pulled out Derek’s cock, half-hard in his hand as he licked up its growing length, humming as he looked up at Derek, sucking at the head. 

“They want you to choke on it,” Derek told him. Stiles closed his eyes, knowing that he could do it, take Derek down his throat. He taught him how. 

After months, almost a year with Derek, Stiles conditioned himself to be able to take Derek’s cock into his mouth. He gasped for breath as he backed away, wiping away excess spit from his mouth as he panted for breath before taking Derek into his mouth once more. 

“Fuck,” Stiles heard Derek say. It was rare for him to speak out during sex, considering it was usually Stiles doing the cursing, but Derek’s voice made Stiles moan as he cupped his own erection. 

“They want me to fuck you. They want to see you.” 

“Okay,” Stiles said as he sat back. They moved the desk near the bed before they started, so that they could be seen easily. Derek sat on the bed first, spreading his legs so that Stiles could sit between them, resting his back against Derek’s chest, sandwiching Derek’s cock between the two of them. Stiles rid himself of his briefs, his hands on Derek’s thighs as Derek teased at Stiles’ nipples, mouthing at his neck and shoulder until Stiles turned his head enough so that they could kiss. 

Stiles felt precome smearing across his stomach as he remained untouched, Derek’s hand sliding down his chest, his stomach, just shy of his cock. Stiles moaned, shoving his tongue deeper into Derek’s mouth as he dug his fingers into Derek’s thighs, spreading his legs with need. 

Derek ghosted his fingers across Stiles’ erection, making him moan. He hadn’t been touched yet this trip, having had dinner with his father and Derek the night before, when he came home from Berkeley. He missed Derek, missed his touch, and having hundreds of horny people watching brought this to a whole new level for him. If only they knew how desperate for Derek’s cock he really was, maybe they’d know why Stiles was already so close to coming. 

“Come on,” Stiles said against Derek’s lips as Derek finally wrapped his hand around Stiles’ cock, jacking him off agonizingly slowly. Stiles arched his back against him, fucking up into Derek’s fist to get more friction. “Fuck.”

“They want to see your ass as I spread you open.” 

“Oh god,” Stiles said as Derek’s hand left him. They re-situated themselves, kissing before Stiles got to his knees, bending over to show the camera his ass as he wrapped his mouth around Derek’s cock. Derek had lube beside him, which he coated his fingers with, before smearing some around Stiles’ entrance. Stiles moaned, spreading his legs wider as Derek inserted a finger, fucking him with it before adding a second. 

“Oh, yeah, you can take another finger can’t you,” Derek said as Stiles nodded his head. He could take four, but that wasn’t what they were doing now. Derek slipped in a third, and Stiles rocked his hips against the intrusion, his mouth leaving Derek’s cock so he could moan. Derek’s fingers left him without warning, his hands spreading Stiles’ cheeks wide, showing off Stiles’ ass to the camera before brushing a thumb over it. 

“Grab the condom,” Derek said, breaking Stiles out of the trance he put himself in, his mind fuzzy, his body reeling at the feeling of Derek’s hands on him after two weeks of being away at school. 

Stiles got out of the way so that Derek’s cock was in view of the camera as he rolled on the condom. They kissed again before Stiles lay down on the bed longways, his ass in the air as he waited for Derek to pull him closer. 

Derek entered him in one movement, not how he usually did it. Stiles gasped, clinging to the bed sheets as Derek rocked his hips. 

“Shit!” Stiles said, crying out with pleasure as Derek thrust into him relentlessly. Stiles knew he wouldn’t last long, but he couldn’t help but jack himself off as Derek fucked him into the mattress. Derek pinned him down, his arm across Stiles’ back as he leaned over him, his hips pistoning against him. Months ago, Stiles wouldn’t have been able to handle it, it would have been too much, but now, Stiles pushed back against Derek, wanting more. Derek slid up Stiles’ body, pressing a kiss against Stiles’ shoulder before hooking his arms beneath Stiles’, bringing their bodies closer together. 

Derek began thrusting against him slowly, but hard, making Stiles shudder with each movement. He couldn’t budge, couldn’t push back as Derek fucked him. 

“Derek, come shot,” Stiles whispered, knowing he was close. Derek moved them, using his strength to pick Stiles up so that he was kneeling, his back pressed against Derek’s chest as Derek replaced his hand, stroking his cock until he came, shooting out across the bedding. Stiles moved his hips in circles, fucking himself on Derek’s cock as he bent back over. He grabbed hold of the sheets in front of him, using them for leverage as he fucked back against Derek. “Come on, come for me.” 

Derek’s hands were on his ass, spreading his cheeks wide as he watched his own cock disappear between Stiles’ asscheeks. Derek pulled out, making Stiles groan as his head dipped down between his shoulders. His body limp, he let Derek drag him around so that his ass faced the camera once more. 

The sound of Derek taking off the condom made Stiles look back at the computer, wondering what was going on. One look at Derek jacking himself off over Stiles’ ass told him everything: come shot. 

Stiles heard Derek groan as he came over Stiles’ ass and lower back, coating him with it, showing off Stiles’ open, well-fucked hole. Stiles didn’t even turn around as Derek addressed the stream. 

“And that is how well he gets fucked,” Derek said. “So you don’t need to worry about that anymore.” Stiles grinned, burying his face against the sheets as Derek signed them off. 

“So you showed off, huh?” Stiles asked. “Fucked me good and hard.” 

“They thought you couldn’t take it,” Derek said simply, kissing Stiles as he got up, his legs feeling like jelly. “They thought wrong.” 

“Mmm,” Stiles hummed as he smiled through the kiss. “You sure showed them.” 

“You fucking yourself against me, that was new.” 

“I’ve had a lot of practice lately, what with me having to take care of myself.” 

“You’ve always been able to take care of yourself,” Derek said. 

Stiles knew he was right, but he was more than glad that he didn’t have to anymore.

**Notes for the Chapter:**

> I just want to thank my betas again, because they deserve a shout out! thanks to ionsquare, mumblo, robotlauren, and foreverblue-navy! you guys are the best and things for putting up with me :)
> 
> and THANK YOU to everyone who not only read this fic, but kudo'sed, commented, and subscribed! this was my most subscribed to fic to date and I just-- I love this fandom, I love writing sterek and I appreciate how receptive this fandom is. 
> 
> /emotional


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